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US20060287461A1 - Thermoplastic polyurethane containing silane groups - Google Patents

Thermoplastic polyurethane containing silane groups Download PDF

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Publication number
US20060287461A1
US20060287461A1 US10/565,539 US56553904A US2006287461A1 US 20060287461 A1 US20060287461 A1 US 20060287461A1 US 56553904 A US56553904 A US 56553904A US 2006287461 A1 US2006287461 A1 US 2006287461A1
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US
United States
Prior art keywords
thermoplastic polyurethane
silane
process according
radical
tpu
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.)
Abandoned
Application number
US10/565,539
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English (en)
Inventor
Oliver Henze
Sabine Peters
Johann-Diedrich Brand
Christa Hackl
Markus Kraemer
Klaus Hilmer
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BASF SE
Original Assignee
BASF SE
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
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Assigned to BASF AKTIENGESELLSCHAFT reassignment BASF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BRAND, JOHANN-DIEDRICH, HACKL, CHRISTA, HENZE, OLIVER STEFFEN, HILMER, KLAUS, KRAEMER, MARKUS, PETERS, SABINE
Publication of US20060287461A1 publication Critical patent/US20060287461A1/en
Priority to US12/659,629 priority Critical patent/US8541535B2/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0895—Manufacture of polymers by continuous processes
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/83—Chemically modified polymers
    • C08G18/837—Chemically modified polymers by silicon containing compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
    • Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article

Definitions

  • thermoplastic polyurethane in particular fibers or hoses, in particular compressed-air hoses, comprising the following structural unit: R 2 —CO—NH—R—Si(R 1 ) 3-x (OR 1 ) x where:
  • the invention further relates to crosslinked polyurethane obtainable via reaction of the inventive thermoplastic polyurethane with water.
  • the invention further relates to a process for preparing thermoplastic polyurethane which has been silane-modified, modified using organosilicon compounds, i.e. having organosilane groups, and to crosslinkable TPUs thus obtainable, in particular fibers or hoses, in particular compressed-air hoses, and also to the corresponding products crosslinked by way of the silane groups, i.e. the organosilicon groups.
  • Thermoplastics are plastics which remain thermoplastic when repeatedly heated and cooled within the typical temperature range for the processing and use of the material.
  • Thermoplastic is the term used for the property, possessed by a plastic within a temperature range typical of that plastic, of softening repeatedly when heated and hardening repeatedly when cooled, and being capable, in the softened state, of repeated molding via flow in the form of a molding, extrudate, or formed component, to give a semifinished product or to give final products.
  • Thermoplastics are widespread in industry, and take the form of fibers, sheets, foils, moldings, bottles, sheathing, packaging, etc.
  • TPU Thermoplastic polyurethane
  • shoe applications e.g. shoe applications, foils, fibers, skiboots, hoses.
  • thermoplastic processing is at the same time a disadvantage of these materials, because their heat resistance is lower than that of crosslinked polymers. It would therefore be desirable to combine the advantages of thermoplastic processing with those represented by the excellent heat resistance of crosslinked polymers.
  • thermoplastic polyurethane and in particular to develop fibers based on thermoplastic polyurethane, where the polyurethane-comprises silane groups, these materials being obtainable through a simple, rapid, and convenient production process, and having excellent crosslinking properties, and, in particular when used as fibers, having a very good level of properties in the crosslinked state.
  • thermoplastic polyurethanes described at the outset and their crosslinked products of reaction with water.
  • silane in particular means organosilicon compounds.
  • organosilicon compounds are also termed silanes.
  • Silanes used may comprise conventional silanes which have an isocyanate group and have at least one, preferably from one to ten, particularly preferably one, silane group. Preference is given to alkoxysilanes.
  • These silanes may have the following structure: OCN—R—Si(R 1 ) 3-x (OR 1 ) x where:
  • a further object was to develop an improved, simpler, quicker, and more cost-effective process for preparing crosslinkable TPUs, in particular a process for preparing thermoplastic polyurethane which has been silane-modified, i.e. has silane groups.
  • this object is achieved by using, during the preparation of the thermoplastic polyurethane, a silane which has an isocyanate group, preferably a silane which has an isocyanate group and has at least one, preferably from one to ten, particularly preferably one, silane group, particularly preferably a silane of the following formula: OCN—R—Si(R 1 ) 3-x (OR 1 ) x where:
  • the organosilicon compounds which have an isocyanate group preferably comprise at least one of the following compounds: ⁇ -isocyanatopropyltrimethoxysilane, isocyanatomethyltrimethoxysilane, ⁇ -isocyanatopropyltriethoxysilane, and/or isocyanatomethyltriethoxysilane, particularly preferably ⁇ -isocyanato-propyltrimethoxysilane, and/or ⁇ -isocyanatopropyltriethoxysilane.
  • a feature of the inventive process is that the silane group can be introduced directly before the TPU preparation process is complete. There is no requirement for complicated additional steps, such as the reaction of a finished TPU with isocyanates and subsequent reaction of the isocyanate-modified TPU with silanes, e.g. as in the teaching of US 2002/0169255.
  • the silane groups which are integrated into the TPU before the preparation process is complete do not cause premature crosslinking during the further treatment of the TPU prior to the actual shaping process. This is surprising because some TPU processes, such as underwater pelletization, take place if appropriate in the presence of moisture, and may be followed by high-temperature drying. These conditions with moisture and heat usually promote the crosslinking reaction of the silanes, whereas this is undesirable until the actual shaping is complete, i.e. after extrusion, injection molding, or spinning.
  • the silanes may be incorporated before the process of preparing the TPUs has been completed.
  • Use may be made here of silanes which have one isocyanate group. Even when use is made of silanes which have one isocyanate group, these “monofunctional” isocyanates do not have any substantial adverse effect on the process of preparing the TPUs.
  • thermoplastic polyurethane is preferably prepared via reaction of (a) isocyanates, and also silane which has an isocyanate group, with (b) compounds reactive toward isocyanates and having a molar mass of from 500 to 10000, and with (c) chain extenders having a molar mass of from 50 to 499, if appropriate in the presence of (d) catalysts, and/or of (e) conventional additives, where the ratio of the entirety of the isocyanate groups in component (a) to the entirety of the functions present in components (b) and (c), and also, if appropriate, (d) and (e), and reactive toward isocyanates is from 0.9:1 to 1.1:1, particularly preferably from 0.95:1 to 1.05:1, in particular 1:1.
  • the ratio here of the entirety of the isocyanate groups in component (a) and of the isocyanate groups in the silanes to the entirety of the functions present in components (b) and (c), and also, if appropriate, (d) and (e), and reactive toward isocyanates is from 0.91:1 to 1.4:1, particularly preferably from 0.96:1 to 1.3:1, in particular from 1.05:1 to 1.25:1.
  • the silanes which have an isocyanate group are preferably regarded as additive for the purposes of the index, i.e. that the total index selected has been raised by the isocyanate groups of the silanes which have an isocyanate group.
  • the inventive crosslinkable TPUs may also be prepared by reacting thermoplastic polyurethane with silane which has an isocyanate group.
  • the silanes which have an isocyanate group are linked to a previously prepared TPU.
  • the TPU preferably in a molten or softened state, particularly preferably in a molten state, may, by way of example, be reacted in an extruder with the silane.
  • the silane groups are preferably integrated into the TPU before preparation of the TPU has been completed.
  • the molar ratio of the isocyanates (a) to the silanes is preferably from 1:0.01 to 1:0.50.
  • Thermoplastic polyurethane is preferably a polyurethane-based thermoplastic elastomer.
  • Thermoplastic polyurethane used in particular comprises TPUs whose Shore hardness is from 50 A to 80 D. Preference is moreover given to TPUs having:
  • TPU in the uncrosslinked state, i.e. with no crosslinking by way of the silane groups.
  • TPUs are generally prepared by reacting (a) isocyanates with (b) compounds reactive toward isocyanates and usually having a molar mass (M w ) of from 500 to 10000, preferably from 500 to 5000, particularly preferably from 800 to 3000, and with (c) chain extenders having a molar mass of from 50 to 499, if appropriate in the presence of (d) catalysts, and/or (e) conventional additives.
  • M w molar mass
  • chain extenders having a molar mass of from 50 to 499, if appropriate in the presence of (d) catalysts, and/or (e) conventional additives.
  • silanes As previously described at the outset, according to the invention use is also preferably made of the silanes.
  • the starting components and processes for preparing the preferred polyurethanes will be described below by way of example.
  • the components (a), (b), and (c), and also, if appropriate, (d) and/or (e) usually used in preparing the polyurethanes will be described below by way of example:
  • the polyetherols used may also comprise what are known as low-unsaturation polyetherols.
  • low-unsaturation polyols are in particular polyether alcohols whose content of unsaturated compounds is less than 0.02 meg/g, preferably less than 0.01 meg/g.
  • polyether alcohols are mostly prepared by addition reactions of alkylene oxides, in particular ethylene oxide, propylene oxide and mixtures of these onto triols or diols described above in the presence of high-activity catalysts.
  • high-activity catalysts are cesium hydroxide and multimetal cyanide catalysts, also termed DMC catalysts.
  • DMC catalyst often used is zinc hexacyanocobaltate.
  • the DMC catalyst may be left in the polyether alcohol after the reaction, but is usually removed, for example by sedimentation or filtration.
  • polybutadienediols with a molar mass of from 500 to 10000 g/mol, preferably from 1000 to 5000 g/mol, in particular from 2000 to 3000 g/mol.
  • TPUs prepared using these polyols can be radiation-crosslinked after thermoplastic processing. This gives better combustion rate behavior, for example.
  • Components a) to c) are particularly preferably difunctional compounds, i.e. diisocyanates (a), difunctional polyols, preferably polyetherols (b), and difunctional chain extenders, preferably diols.
  • chain regulators usually having a molar mass of from 31 to 3000.
  • These chain regulators are compounds which have only one functional group reactive toward isocyanates, examples being monofunctional alcohols, monofunctional amines, and/or monofunctional polyols. These chain regulators can be used for precise adjustment of flow behavior, in particular in the case of TPUs.
  • the amount which may generally be used of chain regulators is from 0 to 5 parts by weight, preferably from 0.1 to 1 part by weight, based on 100 parts by weight of component b), these compounds being defined as part of component (c).
  • the molar ratios of the structural components (b) and (c) may be varied relatively widely in order to adjust the hardness of the TPUs.
  • Molar ratios which have proven successful are from 10:1 to 1:10, in particular from 1:1 to 1:4, this being the ratio of component (b) to the entire amount to be used of chain extenders (c), and the hardness of the TPUs rises here as content of (c) increases.
  • the TPUs may be prepared continuously by the known processes, such as those using reactive extruders or the belt process, by the one-shot method or the prepolymer method, or batchwise by the known prepolymer process.
  • the components to be reacted: (a), (b), (c), and, if appropriate, (d) and/or (e) may be mixed with one another in succession or simultaneously, whereupon the reaction immediately begins.
  • the structural components (a), (b), (c), and also, if appropriate, (d) and/or (e) are introduced into the extruder individually or in the form of a mixture, e.g. at temperatures of from 100 to 280° C., preferably from 140 to 250° C., and are reacted.
  • the resultant TPU is usually extruded, cooled, and pelletized.
  • the TPU may, if appropriate, be modified by compounding in an extruder.
  • this compounding can modify the melt index of the TPU, or its pellet shape, to comply with the requirements.
  • TPUs prepared according to the invention which usually take the form of pellets or powder, to give injection-molded or extruded items, e.g. the desired foils, moldings, rollers, fibers, automotive trim, hoses, cable plugs, folding bellows, drag cables, cable sheathing, gaskets, drive belts, or damping elements.
  • injection molding or extruded items may also be composed of compounded materials comprising the inventive TPU and at least one other thermoplastic, particularly a polyethylene, polypropylene, polyester, polyether, polystyrene, PVC, ABS, ASA, SAN, polyacrylonitrile, EVA, PBT, PET, polyoxymethylene.
  • the TPU prepared according to the invention may be used to produce the items described at the outset.
  • Other processes which may be used are the known powder-slush process, or calendering.
  • the silane-modified thermoplastic polyurethane is preferably spun by well-known methods to give fibers or extruded to give hoses, in particular compressed-air hoses, and the thermoplastic polyurethane is then preferably crosslinked by way of the silane groups, by means of moisture, if appropriate using a catalyst which accelerates the crosslinking process.
  • the crosslinking reactions by way of and through the silane groups are well-known and familiar to the person skilled in the art. This crosslinking usually takes place through moisture, and may be accelerated by heat or by catalysts known for this purpose, e.g. Lewis acids, Lewis bases, Brönsted bases, Brönsted acids.
  • the catalyst used for the crosslinking process preferably by means of moisture, preferably comprises acetic acid, organometallic compounds, such as titanic esters, iron compounds, e.g. ferric acetylacetonate, tin compounds, e.g. stannous diacetate, stannous dioctoate, stannous dilaurate, or the dialkyltin salts of aliphatic carboxylic acids, such as dibutyltin diacetate, dibutyltin dilaurate. Particularly preferred compounds are stannous dilaurate and/or acetic acid.
  • organometallic compounds such as titanic esters, iron compounds, e.g. ferric acetylacetonate
  • tin compounds e.g. stannous diacetate, stannous dioctoate, stannous dilaurate
  • dialkyltin salts of aliphatic carboxylic acids such as dibutyltin diacetate, dibut
  • the product crosslinked by way of the silane groups in partiuclar fibers based on thermoplastic polyurethane crosslinked by way of silane groups, preferably has the following advantages:
  • the heat distortion temperature is an important measure of the quality of an elastomer fiber. Surprisingly, it has been found that the heat distortion temperature of the melt-spun fiber crosslinked by way of silane groups was significantly improved.
  • the HDT of a fiber without inventive silane crosslinking is 120° C. (heat distortion temperature measured with 0.04 mN/dtex pre-tension; heating rate 10 K/min; test range from ⁇ 100 to 250° C.).
  • the HDT could be increased to 173° C. as a result of the crosslinking through the silane groups.
  • fibers based on the crosslinked inventive TPUs whose heat distortion temperature is above 140° C., preferably above 160° C., particularly preferably above 170° C., in particular from 171 to 260° C., measured with 0.04 mN/dtex pre-tension; heating rate 10 K/min, and test range from ⁇ 100 to 250° C.
  • inventive crosslinking of melt-spun elastomer fibers is improvement in resistance toward conventional spinning preparations. Contact with spinning preparations here causes attack, and sometimes complete breakdown of melt-spun fibers without inventive crosslinking, even at low temperatures ( ⁇ 120° C.), whereas inventive crosslinked fibers exhibit almost no damage even at temperatures above 190° C.
  • Elastollan® E 1195 A a TPU from Elastogran GmbH, was kneaded at 210° C. for 3 minutes in a twin-screw mixer. From 5 to 10% by weight of ⁇ -isocyanatopropyltrimethoxysilane were then added, and kneading was continued at 210° C. for a further 6 minutes. The melt was cooled.
  • Elastollan® E 1195 A a TPU from Elastogran GmbH, was placed in a twin-screw mixer and kneaded for 3 minutes at 210° C. 1 percent by weight of SDO was then added and the material was kneaded at 210° C. for a further 6 minutes. The melt was cooled.
  • Elastollan® C 78 A a TPU from Elastogran GmbH, was placed in a twin-screw mixer and kneaded for 3 minutes at 210° C. 1 percent by weight of SDO was then added and the material was kneaded at 210° C. for a further 6 minutes. The melt was cooled.
  • the materials obtained in examples 1, 2, and 3 were aged for 8-48 hours at 80° C. in an acidic solution (pH from 4 to 5). After this, more than 70% of the material was insoluble in DMF, and crosslinking had therefore taken place.
  • the materials 4, 5, 6, and 7 were aged for 848 hours at 80° C. in water. After this, more than 80% of the material was insoluble in DMF, and crosslinking had therefore taken place.
  • the crosslinked TPU exhibited a higher level of stress/strain performance.
  • the crosslinked TPU exhibits higher Shore A hardness values, higher modulus of elasticity values, and a higher Vicat point.
  • the specimens according to example 3 were subjected to a hot-set test (based on EN 60811-2-1). The specimens were in each case loaded with various weights, using a cross section of 1 cm 2 at 180° C. 180° C./100 g 180° C./200 g 180° C./300 g 180° C./400 g ⁇ -Isocyanatopropyltrimethoxysilane 1st test 2nd test 1st test 2nd test 1st test 2nd test 1st test 2nd test 1st test 2nd test 1st test 2nd test % % % % % % % 0 break-off break-off break-off break-off occurred occurred occurred occurred occurred occurred occurred occurred 5 15 0 20 10 20 10 30 10
  • Fibers melt-spun from the TPUs having 5% of ⁇ -isocyanatopropyltrimethoxysilane have the following properties: HDT of 173° C. (heat distortion temperature, measured with pre-tension of 0.04 mN/dtex; heating rate 10 K/min; test range from 100° C. to 250° C.).

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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)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
US10/565,539 2003-07-25 2004-07-09 Thermoplastic polyurethane containing silane groups Abandoned US20060287461A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/659,629 US8541535B2 (en) 2003-07-25 2010-03-15 Thermoplastic polyurethane containing silane groups

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE103342655 2003-07-25
DE10334265A DE10334265A1 (de) 2003-07-25 2003-07-25 Thermoplastisches Polyurethan enthaltend Silangruppen
PCT/EP2004/007568 WO2005014683A1 (de) 2003-07-25 2004-07-09 Thermoplastisches polyurethan enthaltend silangruppen

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/007568 A-371-Of-International WO2005014683A1 (de) 2003-07-25 2004-07-09 Thermoplastisches polyurethan enthaltend silangruppen

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US12/659,629 Continuation US8541535B2 (en) 2003-07-25 2010-03-15 Thermoplastic polyurethane containing silane groups

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US20060287461A1 true US20060287461A1 (en) 2006-12-21

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US12/659,629 Active 2026-04-25 US8541535B2 (en) 2003-07-25 2010-03-15 Thermoplastic polyurethane containing silane groups

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US (2) US20060287461A1 (de)
EP (1) EP1651694B1 (de)
CN (1) CN1829753A (de)
AT (1) ATE512178T1 (de)
DE (1) DE10334265A1 (de)
WO (1) WO2005014683A1 (de)

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US20080308807A1 (en) * 2007-06-15 2008-12-18 Shunpei Yamazaki Display device and manufacturing method thereof
US20090008645A1 (en) * 2007-07-06 2009-01-08 Semiconductor Energy Laboratory Co., Ltd. Light-emitting device
US20100016537A1 (en) * 2005-06-23 2010-01-21 Wacker Chemie Ag Continuous polymer-analogous reaction of reactive silane monomers with functionalized polymers
US20100331480A1 (en) * 2008-01-10 2010-12-30 Henkel Ag & Co. Kgaa Hardenable compositions containing soft-elastic silylated polyurethanes
US8093112B2 (en) 2007-07-20 2012-01-10 Semiconductor Energy Laboratory Co., Ltd. Method for manufacturing display device
CN117659390A (zh) * 2024-02-01 2024-03-08 深圳东创技术股份有限公司 一种热塑性聚氨酯材料及其制备方法

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DE602006006663D1 (de) * 2005-03-24 2009-06-18 Medtronic Inc Modifizierung von thermoplastischen polymeren
EP3655454B1 (de) 2017-07-20 2023-06-07 Basf Se Thermoplastisches polyurethan
CN108034224A (zh) * 2017-12-19 2018-05-15 滁州环球聚氨酯科技有限公司 一种叉车轮毂表面包覆的聚氨酯层制备方法
CN109535374B (zh) * 2018-11-28 2021-05-11 厦门誉匠复合材料有限公司 一种聚氨酯弹性体及其制备方法
CN113910730A (zh) * 2021-10-13 2022-01-11 苏州康乐兴电子有限公司 复合塑料的制备方法
CN115505199A (zh) * 2022-10-11 2022-12-23 深圳市昊昌塑胶有限公司 电线护套、电线护套用复合材料及其制备方法
CN116606541B (zh) * 2023-05-15 2024-10-18 美瑞新材料股份有限公司 一种高强度耐脏污tpu材料及其制备方法

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Publication number Priority date Publication date Assignee Title
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US8101704B2 (en) 2005-06-23 2012-01-24 Wacker Chemie Ag Continuous polymer-analogous reaction of reactive silane monomers with functionalized polymers
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WO2005014683A1 (de) 2005-02-17
US20100209643A1 (en) 2010-08-19
CN1829753A (zh) 2006-09-06
EP1651694A1 (de) 2006-05-03
DE10334265A1 (de) 2005-02-24
ATE512178T1 (de) 2011-06-15
EP1651694B1 (de) 2011-06-08
US8541535B2 (en) 2013-09-24

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