ES2298532T5

Polymeric compositions containing polymers and ionic liquids

Abstract

Polymeric composition, which contains at least one at least partially crystalline polymer without ionic groups and at least one compound with plasticizing properties, the polymeric composition being characterized in that it contains as a plasticizer from 0.1% by weight to 30% by weight of a ionic liquid, the ionic liquid being a salt with a cation, according to the following structures (See formula) meaning R1, R2, R3, R4, R5 and R6, the same or different, hydrogen, an aliphatic, linear or branched hydrocarbyl radical with 1 to 20 carbon atoms, a cycloaliphatic hydrocarbyl radical with 5 to 30 carbon atoms, an aromatic hydrocarbyl radical with 6 to 30 carbon atoms, a alkylaryl radical with 7 to 40 atoms of carbon, an aliphatic, linear or branched hydrocarbyl radical, with 2 to 20 carbon atoms, interrupted by one or more heteroatoms (oxygen, NH, NCH3), an aliphatic, linear or branched hydrocarbyl radical, with 2 to 20 carbon atoms, interrupted by one or more functionalities, selected from the set consisting of -OC (O) -, - (O) CO-, -NH-C (O) -, - (O) C- NH, - (CH3) NC (O) -, - (O) CN (CH3) -, -S (O) 2-O-, -OS (O) 2-, -S (O) 2-NH-, -NH-S (O) 2-, -S (O) 2-N (CH3) -, -N (CH3) -S (O) 2-, an aliphatic, linear or branched hydrocarbyl radical, with 1 to 20 atoms carbon, functionalized at the ends with -OH, -NH2, -N (H) CH3, or a polyether consisting of blocks or statistically, according to the formula - (R 7 -O) nR 8, where R 7 is a linear or branched hydrocarbyl radical, containing from 2 to 4 carbon atoms, where n = from 1 to 30 and meaning R 8 hydrogen, a radical aliphatic hydrocarbyl, linear or branched, with 1 to 20 carbon atoms, a cycloaliphatic hydrocarbyl radical with 5 to 30 carbon atoms, an aromatic hydrocarbyl radical with 6 to 30 carbon atoms, a alkylaryl radical with 7 to 40 carbon atoms, or a -C (O) -R 9 radical with R 9 equal to an aliphatic, linear or branched hydrocarbyl radical with 1 to 20 carbon atoms, a cycloaliphatic hydrocarbyl radical with 5 to 30 carbon atoms, an aromatic hydrocarbyl radical with 6 to 30 carbon atoms, or an alkylaryl radical with 7 to 40 carbon atoms; and with an anion, selected from the set consisting of halides, phosphate; halogen phosphates, alkyl phosphates; nitrate; sulfate, hydrogen sulfate; alkyl sulfates; aryl sulfates; perfluorinated alkyl and aryl sulfates; sulfonate, alkyl sulfonates, aryl sulfonates; perfluorinated alkyl- and aryl sulfonates; perchlorate; tetrachloroaluminate; tetrafluoroborate; alkyl borates; tosylate; saccharinate; alkyl carboxylates and anions of bis (perfluoroalkyl sulfonyl) amide; or a mixture of several such salts.

ES2298532T5, drawing sheet 1 — Sheet 1 of 12

Term

Term ended

Projected expiry passed 13 June 2023, 3.3 years ago.

26 claims: 13 independent, 13 dependent

1
ES 2 298 532 T5 REIVINDICACIONES 1. Composición polimérica, que contiene por lo menos un polímero al menos parcialmente cristalino sin grupos iónicos y por lo menos un compuesto con propiedades plastificantes, estando caracterizada la composición polimérica porque 5 contiene como plastificante de 0,1 % en peso a 30 % en peso de un líquido iónico, siendo el líquido iónico una sal con un catión, de acuerdo con las siguientes estructuras 10 significando R1, R2, R3, R4, R5, iguales o diferentes, hidrógeno, un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, un radical hidrocarbilo cicloalifático con 5 a 30 átomos de carbono, un radical hidrocarbilo aromático con 6 a 30 átomos de carbono, un radical alquilarilo con 7 a 40 átomos de carbono, un radical hidrocarbilo alifático, lineal o ramificado, con 2 a 20 átomos de carbono, interrumpido por uno o varios heteroátomos (oxígeno, NH, NCH3), un radical hidrocarbilo alifático, lineal o ramificado, con 2 a 20 átomos de carbono, interrumpido por una o varias 15 funcionalidades, seleccionadas entre el conjunto formado por -O-C(O)-, -(O)C-O-, -NH-C(O)-, -(O)C-NH, -(CH3)N-C(O)-, ES 2 298 532 T5 -(O)C-N(CH3)-, -S(O)2-O-, -O-S(O)2-, -S(O)2-NH-, -NH-S(O)2-, -S(O)2-N(CH3)-, -N(CH3)-S(O)2-, un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, funcionalizado en los extremos con -OH, -NH2, -N(H)CH3, o un poliéter constituido por bloques o estadísticamente, de acuerdo con la fórmula -(R 7 -O)n-R 8 , siendo R 7 un radical hidrocarbilo lineal o ramificado, que contiene de 2 a 4 átomos de carbono, siendo n = de 1 a 30 y significando R 8 hidrógeno, un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, un radical hidrocarbilo cicloalifático con 5 a 30 átomos de carbono, un radical hidrocarbilo aromático con 6 a 30 átomos de carbono, un radical alquilarilo con 7 a 40 átomos de carbono, o un radical -C(O)-R 9 con R 9 igual a un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, un radical hidrocarbilo cicloalifático con 5 a 30 átomos de carbono, un radical hidrocarbilo aromático con 6 a 30 átomos de carbono, o un radical alquilarilo con 7 a 40 átomos de carbono;y con un anión, seleccionado entre el conjunto que se compone de halogenuros, fosfato;alquil-fosfatos;nitrato;sulfato, hidrógeno-sulfato;alquil-sulfatos;aril-sulfatos;alquil- y aril-sulfatos perfluorados;sulfonato, alquil-sulfonatos, arilsulfonatos;aril-sulfonatos perfluorados;perclorato;tetracloroaluminato;alquil-boratos;tosilato;sacarinato;alquilcarboxilatos;o una mezcla de varias de tales sales.
2
Composición polimérica de acuerdo con la reivindicación 1, estando caracterizada la composición polimérica porque contiene de 0,5 % en peso a 25 % en peso de un líquido iónico.
3
Composición polimérica de acuerdo con la reivindicación 1 o 2, estando caracterizada la composición polimérica porque como polímero por lo menos parcialmente cristalino, contiene por lo menos un polímero elaborable en condiciones termoplásticas, seleccionado entre el conjunto formado por las (co)poliamidas, los (co)poliésteres, los poliuretanos, los poli(fenilen-éteres), las poliolefinas, las (co)poli(éter-amidas), las poli(aramidas), las poli(éter(éter)cetonas) y las poli(éter-éster-amidas).
4
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 3, estando caracterizada la composición polimérica porque como polímero por lo menos parcialmente cristalino contiene por lo menos un polímero reticulado o por lo menos un polímero que se ha de reticular, seleccionado entre el conjunto formado por las (co)poliamidas, los (co)poliésteres, los poliuretanos o los poli(fenilen-éteres).
5
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 4, caracterizada porque el polímero es lineal o ramificado.
6
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 5, estando caracterizada la composición polimérica porque contiene por lo menos una mezcla de polímeros y/o por lo menos una mezcla preparada de polímeros.
7
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 6, caracterizada porque el líquido iónico contiene un anión exento de halógenos, seleccionado entre el conjunto que se compone de fosfato, alquil-fosfatos, nitrato, sulfato, alquil-sulfatos, aril-sulfatos, sulfonato, alquil-sulfonatos, arilsulfonatos, alquil-boratos, tosilato, sacarinato y alquil-carboxilatos.
8
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 7, caracterizada porque el líquido iónico de la composición polimérica contiene diferentes aniones.
9
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 8, estando caracterizada la composición polimérica porque tiene propiedades microbicidas.
10
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 9, estando caracterizada la composición polimérica porque tiene propiedades antiestáticas.
11
Composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 10, ES 2 298 532 T5 estando caracterizada la composición polimérica porque, en comparación con un polímero sin ningún líquido iónico, tiene una temperatura de transición vítrea más baja en hasta 18 K, medida de acuerdo con una calorimetría por barrido diferencial (DSC).
12
Procedimiento para la producción de una composición polimérica, que contiene por lo menos un 5 polímero sin grupos iónicos y por lo menos un compuesto con propiedades plastificantes, conteniendo la composición polimérica como plastificante de 0,1 % en peso a 30 % en peso de un líquido iónico, caracterizado porque primeramente un líquido iónico, siendo el líquido iónico una sal con un catión, de acuerdo con las siguientes estructuras, significando R1, R2, R3, R4, R5, iguales o diferentes, hidrógeno, un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, un radical hidrocarbilo cicloalifático con 5 a 30 átomos de carbono, un radical hidrocarbilo aromático con 6 a 30 átomos de carbono, un radical alquilarilo con 7 a 40 átomos de carbono, un radical hidrocarbilo alifático, lineal o ramificado, con 2 a 20 átomos de carbono, interrumpido por uno o varios heteroátomos (oxígeno, NH, 15 NCH3), un radical hidrocarbilo alifático, lineal o ramificado, con 2 a 20 átomos de carbono, interrumpido por una o varias ES 2 298 532 T5 funcionalidades, seleccionadas entre el conjunto formado por -O-C(O)-, -(O)C-O-, -NH-C(O)-, -(O)C-NH, -(CH3)N-C(O)-, -(O)C-N(CH3)-, -S(O)2-O-, -O-S(O)2-, -S(O)2-NH-, -NH-S(O)2-, -S(O)2-N(CH3)-, -N(CH3)-S(O)2-, un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, funcionalizado en los extremos con -OH, -NH2, -N(H)CH3, o un poliéter constituido por bloques o estadísticamente, de acuerdo con la fórmula -(R 7 -O)n-R 8 , siendo R 7 un radical hidrocarbilo lineal o ramificado, que contiene de 2 a 4 átomos de carbono, siendo n = de 1 a 30 y significando R 8 hidrógeno, un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, un radical hidrocarbilo cicloalifático con 5 a 30 átomos de carbono, un radical hidrocarbilo aromático con 6 a 30 átomos de carbono, un radical alquilarilo con 7 a 40 átomos de carbono, o un radical -C(O)-R 9 siendo R 9 igual a un radical hidrocarbilo alifático, lineal o ramificado, con 1 a 20 átomos de carbono, un radical hidrocarbilo cicloalifático con 5 a 30 átomos de carbono, un radical hidrocarbilo aromático con 6 a 30 átomos de carbono, o un radical alquilarilo con 7 a 40 átomos de carbono;y con un anión, seleccionado entre el conjunto que se compone de halogenuros, fosfato;alquil-fosfatos;nitrato;sulfato, hidrógeno-sulfato;alquil-sulfatos;aril-sulfatos;alquil- y aril-sulfatos perfluorados;sulfonato, alquil-sulfonatos, arilsulfonatos;aril-sulfonatos perfluorados;perclorato;tetracloroaluminato;alquil-boratos;tosilato;sacarinato;alquilcarboxilatos;o una mezcla de varias de tales sales, se pone en contacto con un componente polimérico de la composición polimérica, y a continuación el líquido iónico se distribuye en la composición polimérica.
13
Procedimiento de acuerdo con la reivindicación 12, caracterizado porque se produce una composición polimérica de acuerdo con una de las reivindicaciones 1 a 11.
14
Procedimiento de acuerdo con la reivindicación 12 o 13, caracterizado porque la distribución del líquido iónico en la composición polimérica se efectúa mediante un proceso de mezcladura.
15
Procedimiento de acuerdo con por lo menos una de las reivindicaciones 12 a 14, caracterizado porque el líquido iónico se pone en contacto y se mezcla a fondo con una fase líquida fundida del componente polimérico.
16
Procedimiento de acuerdo con la reivindicación 15, caracterizado porque la mezcladura de los componentes de la composición polimérica se lleva a cabo en una amasadora de 1 o 2 árboles, presentándose el componente polimérico en el estado fundido.
17
Procedimiento de acuerdo con por lo menos una de las reivindicaciones 12 a 14, caracterizado porque el líquido iónico se pone en contacto con una fase sólida del componente polimérico y después de la fusión se mezcla a fondo.
18
Procedimiento de acuerdo con la reivindicación 12 o 13, caracterizado porque la distribución del líquido iónico en la composición polimérica se efectúa mediante difusión.
19
Procedimiento de acuerdo con la reivindicación 18, caracterizado porque la producción se efectúa mediante impregnación de polvos poliméricos por medio de un líquido iónico.
20
Procedimiento de acuerdo con por lo menos una de las reivindicaciones 12 a 14, caracterizado porque por lo menos un polímero y/o un líquido iónico se emplea disuelto en un disolvente.
21
Procedimiento de acuerdo la reivindicación 20, ES 2 298 532 T5 caracterizado porque el disolvente es separado de una etapa precursora de la composición polimérica mediante un procedimiento térmico de separación.
22
Procedimiento de acuerdo la reivindicación 20, caracterizado porque el disolvente es separado de una etapa precursora de la composición polimérica mediante precipitación de la composición polimérica.
23
Utilización de una composición polimérica de acuerdo con una de las reivindicaciones 1 a 11 o de una composición polimérica producida de acuerdo con un procedimiento según una de las reivindicaciones 12 a 22, como pegamento fusible, agente mediador de adherencia, aglutinante, material de carga, material de envasado, agente mejorador de la compatibilidad para la producción de mezclas preparadas de polímeros, agentes modificadores de la viscosidad y/o de la solubilidad en mezclas o composiciones poliméricas, o para la producción de láminas, películas, revestimientos, membranas y cuerpos moldeados, efectuándose la conformación mediante moldeo por inyección, extrusión o moldeo por soplado.
24
Pegamento fusible que contiene una composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 11 o una composición polimérica producida de acuerdo con un procedimiento según una de las reivindicaciones 12 a 22.
25
Aglutinante que contiene una composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 11 o una composición polimérica producida de acuerdo con un procedimiento según una de las reivindicaciones 12 a 22.
26
Artículo deportivo que contiene una composición polimérica de acuerdo con por lo menos una de las reivindicaciones 1 a 11 o una composición polimérica producida de acuerdo con un procedimiento según una de las reivindicaciones 12 a 22.

Independent claims26

103 paragraphs in 9 sections, as filed

ES 2 298 532 T5

DESCRIPTION

Polymeric compositions based on polymers and ionic liquids

The present invention relates to a polymer composition, containing at least one at least partially crystalline polymer without ionic groups and at least one compound with plasticizing properties, the polymer composition as plasticizer having from 0.1% by weight to 30% by weight of an ionic liquid, as well as a process for its production, as well as its use.

For several years now, ionic liquids have been the subject of different research works. As an ionic liquid it is generally understood a liquid, which is composed exclusively of ions. As a demarcation with the classical concept of the melt of salts, in which case it is usually a medium with a high melting point, highly viscous and in most cases highly corrosive, ionic liquids are already liquid and relatively little viscous at low temperatures (<100 ° C). Even though there are some examples, in which the melts of salts at high temperatures were used successfully as reaction media in preparation applications, however only the fact that ionic liquids are present in the liquid state already at some temperatures below 100 ° C, allows its use as a replacement for conventional organic solvents in chemical processes. Even though ionic liquids have been known since 1914, they have nevertheless been intensively investigated as solvents and / or catalysts in organic syntheses only in the last 10 years (KR Seddon compendium article in J.Chem. Technol. Biotechnol 68 (1997), 351-356; T. Welton in Chem. Rev. 99 (1999), 2071-2083; JD Holbrey, KR Seddon in Clean Products and Processes 1 [Clean Products and Processes] (1999) 223-236 ; P. Wasserscheid, W. Keim in Angew, Chem. 112 (2000), 3926-3945 and R. Sheldon in Chem. Comm. (2001), 2399-2407).

S. Fischer et al. Report in ACS Symp. Ser. 737 (1999), 143-150 on inorganic salt hydrate melts, and specifically LÍJ-2H2O, LiClO4-3H2O, NaSCN / KSCN / LiSCN-2H2O and LiClO4'3H2O / Mg (ClO4) 2, as solvents for cellulose.

Polymer extractions with chloroaluminate salts melted at room temperature are the subject of the works of JS Wilkes et al. (Electrochem. Soc. Proceed. (2000) Volume 99-41 (Molten Salts [Molten salts] XII), 65). Mixtures of 1-ethyl-2-methyl-imidazolium chloride and aluminum chloride were used as ionic liquids and various polymers were investigated, including nylon, polyethylene, PVC (polyvinyl chloride) and butyl rubber.

International patent application documents WO 00/16902 and also WO 00/20115 deal with special ionic liquids, which are used as catalysts or as solvents for catalysts in the cases of different organic syntheses.

Both for use as solvents for catalytic reactions and for other fields of use, it may be advantageous to immobilize the ionic liquid. The advantages of immobilization in the cases of catalytic syntheses lie in the simplified separation, production and regeneration of the catalyst and in the less impurization of the products.

Immobilized ionic liquids are known for example from European patent application documents EP-A-0.553.009 and from US patent US-A-5,693,585. Both reference citations describe a calcined support, which works with an ionic liquid, which is composed of aluminum chloride and an alkylated ammonium chloride or imidazolinium chloride. Immobilized ionic liquids are used as catalysts in alkylation reactions.

Document WO-A-01/32308 describes ionic liquids, which are immobilized on a functionalized support, which carries or contains a component of the ionic liquid or a precursor of one of such components. The ionic liquid can be immobilized through the anion by treating a support with an anion source, before the ionic liquid is applied or formed. Alternatively, the ionic liquid can be immobilized, by means of the resource that the cation is fixed by covalent bonds to the support or incorporated into the support. Immobilized ionic liquids are used as catalysts, eg for the Friedel-Crafts reaction.

Also the works of N. Ogata, K. Sanui, M. Rikukawa, S. Yamada, and M. Watanabe (Synthetic Metals 69 (1995), 521-524 and Mat. Res. Soc. Symp. Proc 293, pages 135 and following) deal with "immobilized" ionic liquids and specifically with new polymeric electrolytes, which constitute complexes of polymers capable of conducting ions and are formed by dissolving different polycationic salts in ionic liquids (here also referred to as "Salt melts"), containing aluminum chloride. The polycationic salts may be polyammonium, polypyridinium, polysulfonium and / or polyphosphonium salts. A polymer complex consisting of a polypyridinium salt and, as an ionic liquid, a pyridinium salt and aluminum chloride, was investigated more accurately. The polypyridinium salt constitutes in this case the ionic liquid, instead of the pyridinium salt, and makes it possible for the polymeric complexes to form thin layers, which results from the enormous increase in viscosity compared to that of the ionic liquid. pure. The new polymeric complexes have a high ion-conducting capacity and are of interest, like other polymeric electrolytes, for use in batteries and display devices.

ES 2 298 532 T5

In US-A-6,025,457 polyelectrolytes of the "salt melt" type are disclosed, which contain a polymer of the salt melt type, which is obtained by reaction of an imidazolium derivative, which carries a substituent adjacent to positions 1 and 3, with at least one organic acid or with an organic acid compound, having an acid amide or acid imide bond, with at least one component being realized, i.e. said imidazolium derivative or said organic acid compound is a polymerizable monomer or polymer. Also these polyelectrolytes show a high capacity to conduct ions at room temperature and have good mechanical properties.

Furthermore, many polymeric electrolytes with a high conducting capacity (conductivity), which are composed of a non-ionic polymer in combination with an ionic liquid, have been described in the state of the art.

Thus J. Fuller et al., In J. Electrochem. Soc. 144 (4) (1997), L67-L70, describe gelatinous electrolytes of the rubber type, based on polyvinylidene fluoride and hexafluoropropyl copolymers, and ionic liquids based on triflate or respectively tetrafluoroborate of 1-ethyl-3-methyl-imidazolium.

The Japanese patent application document JP-A-10265673 discloses the production of solid polymer electrolytes in the form of ion-conducting sheets, by means of a polymerization of hydroxyethyl methacrylate and ethylene glycol dimethacrylate, in the presence of an ionic liquid on the surface. 1-butyl-pyridinium tetrafluoroborate base.

The subject of JP-A-10265674 are polymer compositions, for example a polyacrylonitrile and a polyethylene oxide, and ionic liquids. Ionic liquids contain, for example, LiBF4 and 1-ethyl-3-methyl-imidazolium tetrafluoroborate. Solid electrolytes, antistatic agents and shields or protections are indicated as uses.

Noda and collaborators report in Electrochim. Acta 45 (2000), 1265-1270, that certain vinyl monomers can be polymerized in situ in melts, liquid at room temperature, based on 1-ethyl-3-methyl-imidazolium tetrafluoroborate or 1-butyl tetrafluoroborate. -pyridinium, and provide transparent, highly conductive and mechanically stable polymer electrolyte sheets.

Fuller et al. (Molten Salt Forum 5-6 (1998), 605-608) investigated certain mixtures based on ionic liquids or other imidazolium salts and polyvinylidene fluoride and hexafluoropropyl copolymers. These mixtures show high conductivity, high thermal stability and high dimensional stability for applications in batteries, fuel cells or capacitive units such as highly conductive polymer electrolytes.

Watanabe et al. Disclose in Solid State lonics 86-88 (1996), 353-356, that mixtures of salts, liquid at temperatures below 100 ° C, based on trimethylammonium benzoate, lithium acetate and bis (trifluoromethyl Lithium sulfonyl) imide are compatible with poly (acrylonitrile) and poly (vinyl butyral) polymers and provide systems from which film-forming polymeric electrolytes can be produced.

Humphrey et al. (Book of Abstracts, 215th ACS National Meeting, Dallas, March 29 - April 2 (1998), CHED-332, ACSA, Washington DC) describe the dissolution and extraction of polymers with melts of liquid salts at room temperature, based on chloride of aluminum and an organic chloride salt. Ionic liquids can be adjusted for their Lewis acidity and are transformed by addition of hydrogen chloride into superacids.

In Chem. Commun. (2002), 1370-1371, a PMMA is prepared by radical polymerization in an ionic liquid. However, the production of plasticized polymers by polymerization in ionic liquids is not suitable for all types of polymers.

Many polymers, such as, for example, poly (aramides), polyesters, polyamides, poly (ether (ether) ketones), can only be processed with the aid of certain processes or only with difficulties.

In part, the processing under thermoplastic conditions of these polymeric materials as such is not possible, without the occurrence of a decomposition of the polymeric chain. A processing of polymers is made possible in many cases only by introducing plasticizers into the mixtures. For the high temperature region, many of the known plasticizers are not suitable. This may be due, on the one hand, to the too high volatility of the plasticizers or, on the other hand, to an incompatibility with the polymer. In particular for polymers, which have polar groups, such as for example in the case of polyamides or polyesters, it is often not possible to find a suitable plasticizer, which is not corrosive, and which does not emit gases during processing. .

Therefore, the mission of the present invention is to make available a polymeric composition, containing a plasticizer, which improves the properties of at least partially crystalline polymers, which do not have any ionic groups, in particular as regards its processability under thermoplastic conditions, and that it is not volatile or, respectively, only to a small extent, in particular at the processing temperatures of thermoplastic materials, which are current according to the state of the art.

ES 2 298 532 T5

Surprisingly, it was found that polymers, which do not contain any ionic groups, by adding ionic liquids according to claims 1-12, can be improved in terms of their workability, preferably in terms of their workability under thermoplastic conditions , in terms of its electrical properties and in terms of its compatibility with other systems. Even though the use of ionic liquids as catalysts or for the production of polymeric electrolytes has been known for a long time from the bibliography, until now it has not been recognized that the presence of ionic liquids in polymers, which do not have ionic groups, improves the processability under thermoplastic conditions, and therefore ionic liquids can be used as plasticizers. The solution to the problem was all the more surprising, in that it was shown that ionic liquids can also be used as solvents for these polymers, that they are not soluble or are only insufficiently soluble in organic or aqueous solvents, and consequently compositions can be obtained plasticized polymeric.

The object of the present invention, therefore, is a polymer composition according to claim 1 which is composed of at least one at least partially crystalline polymer without ionic groups and of at least one compound with plasticizing properties, the polymer composition containing as a plasticizer from 0.1% by weight to 30% by weight of an ionic liquid.

Furthermore, the object of the invention is a process according to claim 13 for the production of a polymer composition, which contains at least one polymer without ionic groups or at least one compound with plasticizing properties, the polymer composition containing 0 as plasticizer. , 1% by weight to 30% by weight of an ionic liquid.

Furthermore, an object of the invention is the use of a polymer composition according to claim 1, as well as the use of a polymer composition, which had been produced according to the process according to the invention.

The polymer composition according to the invention has the advantage that the solvent-like character of the ionic liquid causes an increase in the flowability of the melts of this polymer composition, the particular advantage being the lack of volatility of the liquid. ionic also at the processing temperatures of the prepared polymer blends. Consequently, either processing temperatures can be used, at which the plasticizers or processing aids used up to now already have too high a vapor pressure and lead to gas emissions and / or coatings of carbon dioxide. the molds or respectively the tools, or the polymers can be processed at lower temperatures by means of the plasticizing effect. This is particularly advantageous in the case of partially crystalline or crystalline polymers, since these, because of their morphology, usually have higher melting temperatures and, linked to this, higher processing temperatures (compared to a amorphous polymer, such as eg PMMA). By using non-volatile plasticizers in the case of partially crystalline or crystalline polymers, it becomes possible to process or use these polymers at higher temperatures. By using ionic liquids as plasticizers, the flowability of polymeric materials in the molten state is increased. Due to their non-volatile and ionic character and their special dissolving properties, ionic liquids can be used as plasticizers or respectively solvents, in particular for polymers or substances, which are not soluble or are only insufficiently soluble in organic or aqueous solvents. When using polymers that are crosslinked or are to be crosslinked in a mixture of substances, the ionic liquid can also be used as a plasticizer, which lowers the glass transition temperature.

The polymer composition according to the invention, which contains at least one at least partially crystalline polymer without ionic groups and at least one compound with plasticizing properties, is distinguished by the fact that the polymer composition contains as plasticizer 0.1% in weight to 30% by weight, preferably from 0.5% by weight to 25% by weight, and especially preferably from 1% by weight to 16% by weight of an ionic liquid. The concentration of the ionic liquid, in the case of polyamide as a polymer that can be processed under thermoplastic conditions, in which the ionic liquid is used as a plasticizer, is preferably 1% by weight to 25% by weight, and preferably 3% by weight to 16% by weight.

The ionic liquid according to the invention contains a salt with a cation, according to the following structures 2 to 9 and 12,

ES 2 298 532 T5

meaning R1, R2, R3, R4, R5, the same or different, hydrogen, an aliphatic hydrocarbyl radical, linear or branched, with 1 to 20 carbon atoms, a cycloaliphatic hydrocarbyl radical with 5 to 30 carbon atoms, an aromatic hydrocarbyl radical with 6 to 30 carbon atoms, an alkylaryl radical with 7 to 40 carbon atoms, an aliphatic hydrocarbyl radical, linear or branched, with 2 to 20 carbon atoms, interrupted by one or more heteroatoms (oxygen, NH, NCH3), an aliphatic hydrocarbyl radical, linear or branched, with 2 to 20 carbon atoms, interrupted by one or more functionalities, selected from the group consisting of -OC (O) -, - (O) CO-, -NH-C (O ) -, - (O) C-NH, - (CH3) NC (O) -, - (O) CN (CH3) -, -S (O) 2-O-, -OS (O) 2-, - S (O) 2-NH-, -NH-S (O) 2-, -S (O) 2-N (CH3) -, -N (CH3) -S (O) 2-, an aliphatic hydrocarbyl radical, linear or branched, with 1 to 20 carbon atoms, functionalized at the ends with -OH, -NH2, -N (H) CH3, or a polyether constituted by blocks or statistically, according to the formula - (R7-O) nR8, where R7 a linear or branched hydrocarbyl radical, containing 2 to 4 carbon atoms, where n = 1 to 30 and R signifying8 hydrogen, a straight or branched aliphatic hydrocarbyl radical with 1 to 20 carbon atoms, a cycloaliphatic hydrocarbyl radical with 5 to 30 carbon atoms, an aromatic hydrocarbyl radical with 6 to 30 carbon atoms, an alkylaryl radical with 7 to 40 carbon atoms, or a radical -C (O) -R9 with R9 equal to a linear or branched aliphatic hydrocarbyl radical with 1 to 20 carbon atoms, a cycloaliphatic hydrocarbyl radical with 5 to 30 carbon atoms, an aromatic hydrocarbyl radical with 6 to 30 carbon atoms, or an alkylaryl radical with 7 to 40 carbon atoms; and with an anion, selected from the group consisting of halides, ie chloride, bromide and iodide, preferably iodide; phosphate; alkyl phosphates; nitrate; sulfate, hydrogen sulfate; alkyl sulfates, preferably octyl

ES 2 298 532 T5 sulfate; aryl sulfates; perfluorinated aryl and alkyl sulfates; sulfonate, alkyl sulfonates, aryl sulfonates; perfluorinated aryl sulfonates, perchlorate; tetrachloroaluminate; alkyl borates, preferably B (C2H5) 3C6Hi3; tosylate; saccharinate; alkylcarboxylates, or a mixture of several such salts.

In a preferred embodiment of the polymer composition according to the invention, the ionic liquid contains halogen-free anions, which are selected from the group consisting of phosphate, alkyl phosphates, nitrate, sulfate, alkyl sulfates, aryl sulfates , sulfonate, alkyl sulfonates, aryl sulfonates, alkyl borates, tosylate, saccharinate and alkyl carboxylates; Alkyl sulfates, in particular octyl sulfate, and tosylate are especially preferred.

In a further preferred embodiment of the polymer composition according to the invention, the ionic liquid contains various anions and / or cations. Ionic liquids, used for example as plasticizers, can therefore be used individually or as a mixture in the polymer composition according to the invention.

The production of the ionic liquid is carried out as described in the bibliography, among other citations, in that of S. Saba, A. Brescia, M. Kaloustian, Tetrahedron Letters 32 (38) (1991), 5031-5034, and in EP 1,072,654 and EP 1,178,106.

Preferably, the polymer composition according to the invention contains at least one polymer that can be processed under thermoplastic conditions, selected from the group consisting of (co) polyamides, (co) polyesters, polyurethanes, poly (phenylene ethers), polyolefins, (co) poly (ether-amides), poly (aramides), poly (ether (ether) ketones) and poly (ester-amides).

In a special embodiment of the polymer composition according to the invention, it contains at least one polymer that can be processed under thermoplastic conditions, selected from the group of homopolyamides. Homopolyamides according to structure 13 or structure 14 are preferred here, where both n> 2 and also k> 2 (independently of one another) and m> 3.

Examples of polymers according to structures 13 and 14 are those of polyamide 46, polyamide 66, polyamide 69, polyamide 612, polyamide 1012, polyamide 1212, polyamide 6, polyamide 11 and polyamide 12.

In a further embodiment of the polymer composition according to the invention, it contains aromatic polyamides based on aromatic dicarboxylic acids and / or aromatic diamines, aromatic polyamides based on terephthalic acid, for example polyamide, are preferred. PA-6,3T, isophthalic acid and naphthalenedicarboxylic acids. Preferably, in this case, the polymer composition according to the invention contains a polymer that can be processed under thermoplastic conditions according to the following structures 15, 16 and 17, where x = from 2 to 22 and y = from 2 to 22;

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In a particularly preferred embodiment of the polymer composition according to the invention, it contains aliphatic polyamides and / or copolyamides. The polyamides of the polymer composition according to the invention have as polyamide-forming monomers, preferably lactams or-aminocarboxylic acids, which contain from 4 to 19, and in particular from 6 to 12, carbon atoms. With particular preference, ε-caprolactam, ε-amino-caproic acid, caprylolactam,,-amino-caprylic acid, laurolactam, ω-amino-decanoic acid and / or o-amino-undecanoic acid are used.

Combinations of a diamine and a dicarboxylic acid are, for example, those of hexamethylenediamine / adipic acid, hexamethylenediamine / dodecanedioic acid, octamethylenediamine / sebacic acid, decamethylenediamine / sebacic acid, decamethylenediamine / dodecanedioic acid / dodecanediocanedioic acid, dodecanediodecamethylenediamine / 2,6 naphthalene-dicarboxylic. In addition to this, however, all other combinations can also be used, such as decamethylenediamine / dodecanedioic acid / terephthalic acid, hexamethylenediamine / adipic acid / terephthalic acid, hexamethylenediamine / adipic acid / caprolactam, decamethylenediamine / dodecanedioic acid ω-amino-undecanoic, decamethylenediamine / dodecanedioic acid / laurolactam, decamethylenediamine / terephthalic acid / laurolactam or dodecamethylenediamine / 2,6-naphthalenedicarboxylic acid / laurolactam.

The polymer composition according to the invention can contain certain copolyamides as a polymer that can be processed under thermoplastic conditions. Those containing base monomers, which lead to the above-mentioned homopolyamides, are preferably suitable for this. As a concomitant component, laurolactam, 11-amino-undecanoic acid, caprolactam, a mixture of adipic acid and hexamethylenediamine, a mixture of dodecanedioic acid and hexamethylenediamine, a mixture of dodecanedioic acid and methylpentanediamine, a mixture of dodecanedioic acid and a decamethylenediamine can be used. mixture of dodecanedioic acid and isophoronadiamine. Such copolyamides are described eg. in German patent documents DE 39 21 164, DE 23 24 160, DE 19 39 758 and DE 32 48 776. The copolyamides mentioned can be used individually or as a mixture for the polymer composition according to the invention. Both homopolyamides and copolyamides can be linear or branched.

The polymer composition according to the invention can contain, as a polymer that can be processed under thermoplastic conditions, certain homo- and / or copolyesters, such as, for example, polyalkylene terephthalates, in particular polyethylene terephthalate and polyethylene terephthalate. butylene), poly (butylene naphthalate), poly (ethylene naphthalate), 1,4-cyclohexanedimethanol (co) polyesters, poly (caprolactone), poly (oxytetramethylene) -b-poly (butylene terephthalate) or polylactides. Preferably, copolyesters according to structure 18 are of this type,

where d = from 2 to 6, e = from 2 to 4, a> 20, b = from 0 to 40, c = from 1 to 40, and the structural units, which are based on monomers that each have two groups hydroxyl, can be linear or branched. Copolyesters according to structure 19 are preferred;

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where g = from 1 to 5, f = from 1 to 5 and Q and S, independently of one another, can be bivalent radicals, e.g. according to structures 20, 21, 22 and 23:

Especially preferred are copolyesters that are formed from different hydroxycarboxylic acids and / or lactones, according to structure 24,

it being possible for both R10 and R11 to be linear or branched alkyl radicals, preferably o> 1 and q <200, and however preferably o> 10 and q <70.

Copolyesters according to structure 25 are very particularly preferred:

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R12 being linear or branched alkyl radicals, which can be either the same or different, R13 being a hydrocarbyl group with 2 to 4 carbon atoms, e.g. - (CH2) 2-, -CH2-CHCH3) - , - (CH2) 4-, and p = 1 to 40. In a special embodiment, different lactones can be used as monomers.

Likewise, preferably, a polymer composition according to the invention may contain polymers that can be processed under thermoplastic conditions, selected from the group of polyolefins, polyurethanes, which can be processed under thermoplastic conditions, poly (phenylene ethers) as described in the EP 0,657,519, copoly (ether-amides) and copoly (ether-ester-amides).

In another embodiment, the polymer composition according to the invention contains at least one crosslinked polymer or at least one polymer to be crosslinked. Preferably, the polymer composition according to the invention contains at least one polymer, selected from the group of (co) polyamides, (co) polyesters, polyurethanes or poly (phenylene ethers). This polymer composition according to the invention makes it possible to produce a polymer that is plasticized and cross-linked with a non-volatile plasticizer, which is ionic liquid.

The polymers contained in the composition according to the invention can be linear or branched. The polymer compositions according to the invention can contain one or more polymers, either in the form of a prepared polymer mixture, a copolymer or a physical mixture, preferably the polymer composition according to the invention contains at least one polymer mixture or at least a prepared blend of polymers. The polymeric component may contain additives, such as, for example, UV (ultraviolet) stabilizing agents, fillers, flame retardants and antioxidants. The polymer composition according to the invention can contain, in a special embodiment, modified polymers, eg end-group modified.

The polymer composition according to the invention preferably has, compared to a polymer without the presence of the ionic liquid, a glass transition temperature that is 18 K lower, measured according to Differential Scanning Calorimetry (DSC). Calorimetry).

Furthermore, the polymer composition according to the invention, which contains a crystalline or partially crystalline polymer, has - compared to the polymer without the presence of the ionic liquid - a higher recrystallization capacity, measured by initiation of recrystallization at a higher temperature. in the case of a DSC cooling test, from the polymer melt.

These morphological properties can improve the workability, in particular the workability under thermoplastic conditions, of the polymer composition according to the invention, compared to a polymer composition without an ionic liquid. This is shown eg in the fact that the polymer composition according to the invention can be molded at lower temperatures, without any decomposition of the polymer chain taking place, or the shaping process can be carried out at higher temperatures, without the plasticizer - in other words, the ionic liquid - be volatile.

The polymer composition according to the invention may additionally have microbicidal properties. These polymer compositions according to the invention with microbicidal properties preferably contain an ionic liquid with a quaternary ammonium ion, particularly preferably TEGOTAIN® 3300, which itself already has microbicidal properties. In a special embodiment of the polymer composition according to the invention, at least one of the polymers used can already have microbicidal properties. Certain polymers which have microbicidal properties are described inter alia in DE 199 52 221, DE 199 43 344 or DE 199 40 023.

Furthermore, the polymer composition according to the invention can additionally have antistatic properties. The antistatic properties can be brought about either by the reaction by addition of water molecules (increased water absorption) and consequently in accordance with the principle of generally known improvement of the conductivity of polymeric materials by the addition of salts, such as e.g. potassium formate, or

ES 2 298 532 T5 can be caused by ionic conductivity, which can be intrinsically associated with one of the ionic liquids added.

In the process according to the invention for the production of a polymer composition, which contains at least one polymer without ionic groups and at least one compound with plasticizing properties, the polymer composition having as plasticizer 0.1% by weight a 30% by weight of an ionic liquid, in particular of the polymer composition according to the invention, preferably the ionic liquid is first contacted with an ionic component of the polymer composition, for example with at least one of the polymers, and then the ionic liquid is distributed in the polymer composition. In this case, one of the components of the polymer composition according to the invention can be present in the molten or solid state, or dissolved in a solvent. If one of the components of the polymer composition according to the invention is used in the dissolved state in a solvent, the solvent can then be separated from the precursor stage of the polymer composition according to the invention, preferably this is carried out by means of a thermal separation process, such as, for example, distillation, or by precipitation of the polymer composition according to the invention, for example, by adding a non-solvent or by lowering the temperature.

In a special embodiment of the process according to the invention, the solvent or swelling agent, which in this case is equal to the ionic liquid, can remain contained in the polymer composition according to the invention. This is especially advantageous in the case of multi-phase polymer systems, in which e.g. Only one of the polymeric components is compatible with the ionic liquid, from this additional new properties can be established for the multi-phase system, preferably along the boundaries between phases. A further possibility of using the polymer composition according to the invention, in which the ionic liquid remains contained, is the dissolution or swelling of one of the polymer components of a multi-phase system, another component of the polymer being incompatible with the liquid. pure ionic. By mixing or kneading this multi-phase system, the ionic liquid can be made to become the phase, which is incompatible with the pure ionic liquid.

In a special embodiment of the process according to the invention, the ionic liquid is distributed in the polymer composition by means of a mixing process. In this case, the ionic liquid can be brought into contact, and then thoroughly mixed, with the molten liquid phase of the polymer component. A further possibility consists in contacting the ionic liquid with the solid phase of the polymeric component, then melting it and afterwards mixing it thoroughly. For example, this can be carried out by mechanical mixing of the polymeric component and the ionic liquid by means of an extruder or stirrer at moderate temperatures, the mixing of the individual components of the polymeric composition according to the invention in a 1- or 2-shaft kneader is preferred. , the polymeric component being present in the molten state. Furthermore, in the case of the mixing process, the polymeric component can be dissolved in the ionic liquid at higher temperatures, or both the polymeric component and the ionic liquid are dissolved in a solvent. In a special embodiment of this partial process step, the polymer component, which contains, for example, a precipitated polymer, spray dried or ground (cold), is mixed with the ionic liquid optionally by adding a solvent for the ionic liquid, which constitutes a non-solvent for the polymeric component, in order to consequently obtain a homogeneous distribution of the ionic liquid in the polymer composition according to the invention.

In another preferred embodiment of the process according to the invention, the ionic liquid is distributed in the polymer composition by diffusion. The impregnation of polymeric powders by means of an ionic liquid is preferred here, and the impregnation of foils, fibers, foams or injection molded parts, using auxiliary substances such as, for example, solvents, is particularly preferred.

The polymer composition according to the invention or the polymer composition produced according to the process according to the invention can be used, for example, in a process for shaping. During shaping, a synthetic material, which contains a polymer composition according to the invention or a polymer composition produced according to a process according to the invention, or is the polymer composition according to the invention itself, can be formed thermally, for example, for example. by injection molding, extrusion or blow molding. In the case of injection molding processing of thermoplastic materials, the polymer materials are in particular good processability. This, in the case of the use of polymers with strongly polar liquids, may be limited due to intra- and intermolecular interactions. By using the polymer compositions according to the invention, or the polymer composition produced according to the process according to the invention, in which cases ionic liquids are used as plasticizers, the interactions between the functional groups attached to the polymers and consequently improved workability is achieved.

The polymer composition according to the invention or the polymer composition produced according to the processes according to the invention can also be used as raw material used in spinning processes. In the case of polymers that have to be spun to form fibers, the ionic liquid can make the spinning process possible or easier. Due to the lowering of the melt viscosity through the addition of ionic liquids, the processing window for the spinning process can be widened; the same is true for sheet production or other extrusion processes.

ES 2 298 532 T5

The ionic liquids contained as plasticizers for processing aids in the polymer compositions according to the invention or respectively in the polymer compositions produced according to the process according to the invention, provided that they are miscible with water or with another solvent incompatible with the polymer, can be extracted again from the polymers after processing, whereby the structure and properties of the polymer can be modified. In this way, new areas of applications can be opened up for individual types of polymers.

A further object of the invention is the use of the polymer composition according to the invention or the polymer composition produced according to the process according to the invention, for the production of foils, films, sports shoes, coatings, preferably in the case of appliances or sporting goods, such as eg the coverings of snowboards (in English snowboards) and membranes. The use of the polymer composition according to the invention or the polymer composition produced according to the processes according to the invention, such as hot-melt adhesives, adhesion media, binders, fillers or packaging material is preferred. . The use of the polymer composition according to the invention or the polymer composition produced according to the processes according to the invention, as adhesion mediating agents, is preferably useful in multi-substance polymer systems, such as, for example, in multilayer tubes. or in composite material systems. In displays or other electronic component parts, the polymer composition according to the invention or the polymer composition produced according to the processes according to the invention can be used as binding agent, filler or as packaging material. . In the production of membranes, preferably ceramic membranes, the polymer composition according to the invention or the polymer composition produced according to the processes according to the invention can be used, and an improvement in effect can be established from this. membrane separator.

The polymer composition according to the invention or the polymer composition produced according to the processes according to the invention can be used as a component part of a mixture of polymers, which are not miscible or not compatible, as a compatibility enhancing agent for production of a ready mix of polymers, preferably homogeneous ready mix of polymers.

In a further use of the polymer composition according to the invention or the polymer composition produced according to the processes according to the invention, it can be used as a viscosity and / or conductivity modifier in polymer compositions or mixtures. In this case, the polymer composition according to the invention or the polymer composition produced according to the processes according to the invention can be used as a so-called masterbatch.

The polymer composition according to the invention or the polymer composition produced according to the processes according to the invention can be used in these applications in admixture with other polymers or directly.

The polymer composition according to the invention or the polymer composition produced according to the processes according to the invention makes it possible to produce new binder or adhesive systems. By means of the presence of ionic groups by means of the ionic liquid, the adhesive behavior of the polymer composition according to the invention or respectively of the polymer composition produced according to the processes according to the invention can be improved to polar or swollen surfaces or incipiently dissolved by ionic liquids.

According to the current state of the art, conductive glue and binder systems are produced by adding special conductive fillers. Antistatic finishes and finishes for molding compounds, varnishes, vulcanized rubbers and foamed materials are produced either by incorporating conductivity-enhancing fillers, fibers, for example carbon black or graphite, or salts. low molecular weight, such as potassium formate. Electrically conductive glues have been introduced in the past as an alternative or respectively as a supplement to soldering materials, in particular in electronics. As base polymers, predominantly epoxy resins are used, in addition glue systems based on cyanoacrylates, silicones and polyimides are known. Gold, silver, copper or nickel in the form of flakes or flakes are known as conductivity-enhancing additives, also eg silver-coated glass beads (EP 0,195,859).

Along with this, regarding the state of the art in the case of polymeric materials finished and prepared to be conductive, it must be mentioned for electronic applications the fact that there are materials, which, either by means of an addition of polymeric materials intrinsically conductive (e.g. a poly (ethoxythiophene) doped with BF4) as an additive for antistatically finished and finished films, heat sealable (DE 42 19 410), or which, with the addition of conductive particles or fibers finished antistatically or respectively conductively, raise the conductivity of the prepared polymer blend.

The adaptation of the electrical properties of the composition according to the invention or respectively of the polymer composition produced according to the processes according to the invention is possible within wide ranges by incorporating the ionic groups by means of the ionic liquids in the

ES 2 298 532 T5 polymer composition. Consequently, an antistatic, or partly also semiconductive, property can be produced from the polymer composition according to the invention or from the polymer composition produced according to the processes according to the invention. The polymer composition according to the invention or the polymer composition produced according to the processes according to the invention can therefore be used in electrical and electronic component parts as binders or semi-conductive or antistatic adhesives for processing by (co-) extrusion. or injection molding. The use of the polymer composition according to the invention or the polymer composition produced according to the processes according to the invention, for example in electronic component parts, can be particularly advantageous because of the varying electrical and thermal properties of these systems.

The following Examples should explain the invention in greater detail, without limiting the extent of its patent protection:

Example: Production of a polymer composition according to the invention g of VESTAMELT, a hot-melt glue based on copolyamides, from Degussa AG, and 15% by weight of an ionic liquid, based on VESTAMELT (which corresponds to 0.75 g of ionic liquid) in 25 g of acetone, they were mixed intimately on a shaker and shaker equipment, and then the acetone was removed on a rotary evaporator.

As ionic liquids, the following were used:

• 1-Ethyl-3-methyl-imidazolinium tosylate • Octyl-trioctyl-ammonium sulfate (Reference Example) • Octyl-1,3-dimethyl-imidazolinium sulfate

As VESTAMELT powders were used:

• VESTAMELT VM 250-P2 • VESTAMELT VM 430-P2 • VESTAMELT VM 470-P830.

The following table reproduces the decrease in the melting temperature or the glass transition temperature and the simultaneous increase in the enthalpies of melts, in comparison with the original powders.

<td>VESTAMELT</td><td>Ionic liquid</td><td>ATm (K)</td><td>ATg (K)</td><td>A (AH) (J / g)</td>

<td>VM250</td><td>Octyl trioctyl ammonium sulfate</td><td> -4,8</td><td>nd</td><td> 14,5</td>

<td rowspan="3">VM430</td><td>1-Ethyl-3-methyl-imidazolinium tosylate</td><td> -5,4</td><td> -14,3</td><td> 16,3</td>

<td>Octyl trioctyl ammonium sulfate *</td><td> -5,7</td><td> -10,0</td><td> 1,7</td>

<td>1,3-dimethyl-imidazolinium octyl sulfate</td><td> -6,0</td><td> -16,6</td><td> 11,5</td>

<td rowspan="2">VM470</td><td>1-Ethyl-3-methyl-imidazolinium tosylate</td><td> -4,0</td><td> -14,9</td><td> 10,3</td>

<td>1,3-dimethyl-imidazolinium octyl sulfate</td><td> -4,5</td><td> -18,0</td><td> 13,6</td>

Reference example

By using ionic liquids as plasticizers, a decrease in the melting temperature as well as the glass transition temperature is achieved, and consequently an improved processing under thermoplastic conditions is made possible.

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10230572	Germany	A	2002-07-05
10230572	Germany	A	2002-07-05
10230572	Germany	–	2002-07-05
10243181	Germany	A	2002-09-18
10243181	Germany	A	2002-09-18
10243181	Germany	–	2002-09-18
DE2002130572	–	–	–
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CA2491587A1	Canada	A1	2004-01-15
WO2004005391A1	World Intellectual Property Organization (WIPO)	A1	2004-01-15
DE10243181A1	Germany	A1	2004-01-22
AU2003281343A1	Australia	A1	2004-01-23
EP1519988A1	European Patent Office (EPO)	A1	2005-04-06
CN1681878A	China	A	2005-10-12
JP2005532440A	Japan	A	2005-10-27
US2006100323A1	United States of America	A1	2006-05-11
EP1519988B1	European Patent Office (EPO)	B1	2008-01-02
AT382655T	Austria	T	2008-01-15
ATE382655T1	Austria	T1	2008-01-15
DE50308930D1	Germany	D1	2008-02-14
ES2298532T3	Spain	T3	2008-05-16
US7601771B2	United States of America	B2	2009-10-13
EP1519988B2	European Patent Office (EPO)	B2	2011-08-17
ES2298532T5This record	Spain	T5	2012-01-10

Polymeric compositions containing polymers and ionic liquids

Abstract

Term

ES 2 298 532 T5

DESCRIPTION

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