Classifications

• • C—CHEMISTRY; METALLURGY
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  • B29B9/00—Making granules
  • B29B9/12—Making granules characterised by structure or composition
• • B—PERFORMING OPERATIONS; TRANSPORTING
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  • B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
  • B29C45/0001—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor characterised by the choice of material
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  • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
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  • B32B5/024—Woven fabric
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  • C08G18/24—Catalysts containing metal compounds of tin
  • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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• • C—CHEMISTRY; METALLURGY
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  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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• • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
  • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
  • F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
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Definitions

• the present invention relates to a thermoplastic polyurethane obtainable or obtained by reacting at least one polyisocyanate composition, 1, 3-propanediol as a chain extender and a polyol composition.
• the present invention relates to a thermoplastic polyurethane obtainable or obtained by reacting at least one polyisocyanate composition, 1,3-propanediol as chain extender and a polyol composition, wherein the polyol composition contains at least polytetrahydrofuran (PTHF) and the polyisocyanate composition comprises at least methylene diphenyl diisocyanate ( MDI).
• PTHF polytetrahydrofuran
• MDI methylene diphenyl diisocyanate
• the present invention relates to a process for the preparation of such thermoplastic polyurethanes, and the use of such polyurethanes for the production of injection molded products, extrusion products, films and molded articles.
• Thermoplastic polyurethanes for various applications are known in principle from the prior art. By varying the starting materials different property profiles can be obtained.
• WO 2006/082183 A1 discloses a process for the continuous preparation of thermoplastically processable polyurethane elastomers, in which a polyisocyanate, a compound having zerevitinoff-active hydrogen atoms having an average molecular weight of 450 g / mol to 5,000 g / mol, a chain extender and other auxiliary and Additives are implemented. Special property profiles are achieved through special processing.
• EP 0 922 552 A1 discloses a process for the continuous production of granules of thermoplastic polyurethane elastomers, wherein first by reacting organic diisocyanates, difunctional polyhydroxyl compounds having molecular weights of 500 to 8000 and difunctional chain extenders having molecular weights of 60 to 400 in the presence of Catalysts and optionally auxiliaries and / or additives granules is produced.
• the use for the production of extrusion, injection molding or calendering, in particular cable sheathing, hoses and / or films is also disclosed.
• EP 0 959 104 A1 discloses blends comprising a thermoplastic polyurethane having a Shore hardness of 60 A to 50 D and ethylene-propylene (EPM) rubbers and / or modified ethylene-propylene (EPM) rubbers, which are also used for the production be used by hoses.
• EPM ethylene-propylene
• EPM modified ethylene-propylene
• thermoplastic polymer obtained by reacting a polyisocyanate, a glycol as a chain extender and a polyether polyol.
• Various isocyanates, chain extenders and polyols are disclosed.
• the properties of the thermoplastic polyurethane can be varied by the nature of the starting materials and the proportions used. For example, for use as a hose material, in particular for pneumatic hoses, a high bursting pressure is required even at elevated temperatures.
• the stability can be influenced. Processing, for example by tempering, can also influence the stability.
• existing ester variants which show a bursting pressure of greater than 20 bar at 70 ° C. are opaque to translucent and thus unsuitable for many applications.
• thermoplastic polyurethane for example, the determined by TMA onset temperature.
• an object of the present invention was accordingly to provide improved materials which show a good bursting pressure even at elevated temperatures in the application for the manufacture of hoses.
• Another object of the present invention was to provide materials with high heat resistance.
• thermoplastic polyurethane obtainable or obtained by reacting at least the components (i) to (iii):
• thermoplastic polyurethane obtainable or obtained by reacting at least the components (i) to (iii):
• thermoplastic polyurethane obtainable or obtained by reacting at least the components (i) to (iii):
• polystyrene resin contains at least polytetrahydrofuran (PTHF) and the polyisocyanate composition contains at least methylene diphenyl diisocyanate (MDI).
• PTHF polytetrahydrofuran
• MDI methylene diphenyl diisocyanate
• 1, 3-propanediol as a chain extender, especially when used as the sole chain extender or in combination with a defined Polyisocyanatzusammen ammen am and a defined polyol composition, a thermoplastic polyurethane is obtained, the behavior of a good Berst réelle- and a has high heat resistance, and preferably is transparent.
• 1,3-propanediol as chain extender, in particular in combination with the defined polyisocyanate composition and the polyol composition, it was possible to produce a hose which has a bursting pressure of greater than 20 bar at 70 ° C., and preferably also transparent is.
• the hoses show a substantially punctiform bursting behavior.
• thermoplastic polyurethane is obtained or is obtainable by reacting the components (i) to (iii).
• a Polyisocyanatzusammen GmbH, a polyol composition and 1, 3-propanediol are implemented as a chain extender.
• 1, 3-propanediol no further chain extender is used.
• the proportion of the 1,3-propanediol used in the amount of chain extender used is greater than 85 mol%. If, in addition to 1,3-propanediol, no further chain extender is used, the proportion of the 1,3-propanediol used in the amount of chain extender used is thus 100 mol%.
• a polyisocyanate composition containing at least methylene diphenyl diisocyanate (MDI) is reacted with a polyol composition containing at least polytetrahydrofuran (PTHF) and 1,3-propanediol as a chain extender.
• MDI methylene diphenyl diisocyanate
• PTHF polytetrahydrofuran
• the polyol composition used contains at least one polyol in the context of the present invention.
• the polyol composition may also contain two or more polyols.
• the polyol composition contains at least one polytetrahydrofuran.
• the polyol composition does not contain polytetrahydrofuran. If the polyol composition is free of polytetrahydrofuran (PTHF), preferably no polytetrahydrofuran (PTHF) is used as further component in the reaction of components (i) to (iii).
• PTHF polytetrahydrofuran
• the polyol composition contains at least one polyol.
• Polyols are generally known to the person skilled in the art and are described, for example, in "Kunststoffhandbuch, Volume 7, Polyurethanes", Carl Hanser Verlag, 3rd edition 1993, Chapter 3.1. Particular preference is given to using polyesterols or polyetherols as polyols. Likewise, polycarbonates can be used. Copolymers can also be used in the context of the present invention.
• the number-average molecular weight of the polyols used according to the invention is preferably between 0.5 ⁇ 10 3 g / mol and 8 ⁇ 10 3 g / mol, preferably between 0.6 ⁇ 10 3 g / mol and 5 ⁇ 10 3 g / mol, in particular between 0.8 ⁇ 10 3 g / mol and 3 x 10 3 g / mol.
• polyethers are suitable, but also polyesters, block copolymers and hybrid polyols, such as e.g. Poly (ester / amide).
• preferred polyetherols are polyethyleneglycols, polypropylene glycols, polyadipates, polycarbonate (diol) s and polycaprolactone.
• the present invention relates to a thermoplastic polyurethane as described above, wherein the polyol used comprises at least one polytetrahydrofuran and at least one polyol selected from the group consisting of polyethylene glycol, polypropylene glycol, polyadipates, polycarbonate (diols) and polycaprolactones ,
• the polyol used has a molecular weight Mn in the range from 500 g / mol to 4000 g / mol, preferably in the range from 800 g / mol to 3000 g / mol.
• the present invention relates to a thermoplastic polyurethane as described above, wherein at least one polyol contained in the polyol composition has a molecular weight Mn in the range of 500 g / mol to 4000 g / mol. According to the invention, it is also possible to use mixtures of different polyols.
• the polyols used or the polyol composition have an average functionality between 1, 8 and 2.3, preferably between 1, 9 and 2.2, in particular 2.
• the polyols used in the invention have only primary hydroxyl groups.
• at least one polyol composition containing at least polytetrahydrofuran is used as component (iii) for the preparation of the thermoplastic polyurethane.
• the polyol composition in addition to polytetrahydrofuran also contain other polyols.
• further polyethers are suitable, but also polyesters, block copolymers and hybrid polyols such as poly (ester / amide).
• Preferred polyetherols according to the invention are polyethyleneglycols, polypropylene glycols and polycaprolactone. Accordingly, according to another embodiment, the present invention relates to a thermoplastic polyurethane as described above, wherein the polyol composition contains at least one polytetrahydrofuran and at least one further polyol selected from the group consisting of polyethylene glycol, polypropylene glycol and polycaprolactone.
• the polytetrahydrofuran has a molecular weight Mn in the range of 750 g / mol to 1400 g / mol.
• composition of the polyol composition can vary widely within the scope of the present invention.
• content of polytetrahydrofuran may be in the range of 15% to 85%, preferably in the range of 20% to 80%, more preferably in the range of 25% to 75%.
• the polyol composition may also contain a solvent. Suitable solvents are known per se to the person skilled in the art.
• the molecular weight Mn of the polytetrahydrofuran is preferably in the range from 650 to 1400 g / mol. More preferably, the molecular weight Mn of the polytetrahydrofuran is in the range of 750 to 1400 g / mol.
• the present invention relates to a thermoplastic polyurethane as described above, wherein the polytetrahydrofuran has a molecular weight Mn in the range of 650 g / mol to 1400 g / mol.
• Mn molecular weight of 650 g / mol to 1400 g / mol.
• the present invention relates to a thermoplastic polyurethane as described above, wherein the polyol composition used is free of polytetrahydrofuran (PTHF) and in the implementation no polytetrahydrofuran (PTHF) is used as a further component.
• the present invention relates to a thermoplastic polyurethane as described above, wherein in addition to 1, 3-propanediol no further chain extender is used, the polyol composition is free of polytetrahydrofuran (PTHF) and in the implementation no polytetrahydrofuran (PTHF) used as another component becomes.
• 1, 3-propanediol can be used alone as a chain extender.
• further chain extenders it is also possible within the scope of the present invention for further chain extenders to be used.
• the proportion of the 1,3-propanediol used in the amount of chain extender used is greater than 85 mol%, preferably is greater than 90 mol%, more preferably greater than 95 mol%, particularly preferably greater than 98 mol%, particularly preferably greater than 99 mol%.
• Suitable further chain extenders are, for example, compounds which have at least two isocyanate-reactive functional groups, for example hydroxyl groups, amino groups or thiol groups.
• the present invention accordingly relates to a thermoplastic polyurethane as described above, wherein at least one further chain extender is used selected from the group consisting of compounds having at least two isocyanate-reactive functional groups.
• 3-propanediol can be used as chain extenders in the context of the present invention, for example, compounds having hydroxyl or amino groups, in particular with two hydroxyl or amino groups.
• the average functionality of the mixture of chain extenders used is preferably two.
• hydroxyl groups in particular diols, as further chain extenders. It is possible with preference to use aliphatic, aliphatic, aromatic and / or cycloaliphatic diols having a molecular weight of from 50 g / mol to 220 g / mol. Preference is given to alkanediols having 2 to 10 C atoms in the alkylene radical, in particular di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona and / or decaalkylene glycols. For the present invention, more preferably 1, 2-ethylene glycol, 1, 4-butanediol, 1, 6-hexanediol. Also, aromatic compounds such as hydroxyquinone (bis (2-hydroxyethyl)) ether can be used.
• the chain extender used in addition to 1,3-propanediol is preferably a diol having a molecular weight Mw ⁇ 220 g / mol.
• the present invention relates to a thermoplastic polyurethane as described above wherein at least one further chain extender selected from the group consisting of aliphatic and aromatic diols, diamines and amino alcohols is used.
• the present invention relates to a thermoplastic polyurethane as described above, wherein at least one further chain extender selected from the group consisting of monoethylene glycol, aminopropanol, 1, 4-butanediol, 1, 6-hexanediol and hydroxyquinone (bis (2-hydroxyethyl) ) ether (HQEE) is used.
• 1,3-propanediol is preferably used alone as a chain extender, ie the polyol composition is also free of further chain extenders, for example free of short-chain diamines or diols, such as diols with a molecular weight Mw ⁇ 220 g / mol.
• the amount of chain extender and polyol composition used can vary within wide limits.
• component (iii) and component (ii) are used in a molar ratio of (iii) to (ii) of 1 to 0.7, 1 to 2.7, and 1 to 7.3.
• a polyisocyanate cyanate composition is used to prepare the thermoplastic polyurethane.
• the polyisocyanate composition contains at least one polyisocyanate.
• the polyisocyanate composition may also contain two or more polyisocyanates.
• a polyisocyanate composition is used which contains at least methylene diphenyl diisocyanate (MDI).
• the term methylene diphenyl diisocyanate means 2,2'-, 2,4'- and / or 4,4'-diphenylmethane diisocyanate or a mixture of two or three isomers.
• 2,2'-, 2,4'- and / or 4,4'-diphenylmethane diisocyanate can be used according to the invention or a mixture of two or three isomers.
• the polyisocyanate composition may also contain further polyisocyanates. According to the invention, it is thus also possible for the isocyanate composition to contain methylene diphenyl diisocyanate and at least one further polyisocyanate. However, according to the invention it is also possible that the isocyanate composition contains only methylene diphenyl diisocyanate.
• a polyisocyanate composition containing no methylenediphenyl diisocyanate (MDI) can also be used to prepare the thermoplastic polyurethane.
• the present invention relates to a thermoplastic polyurethane as described above, wherein the polyisocyanate composition used is free of methylene diphenyl diisocyanate (MDI).
• MDI methylene diphenyl diisocyanate
• the polyisocyanate composition used is free from methylene diphenyl diisocyanate (MDI)
• MDI methylene diphenyl diisocyanate
• Preferred polyisocyanates in the context of the present invention are diisocyanates, in particular aliphatic or aromatic diisocyanates, more preferably aromatic diisocyanates.
• pre-reacted prepolymers can be used as isocyanate components in which some of the OH components are reacted with an isocyanate in an upstream reaction step. These pre- In a subsequent step, the actual polymer reaction, polymers are reacted with the remaining OH components and then form the thermoplastic polyurethane.
• prepolymers offers the possibility to also use OH components with secondary alcohol groups.
• the aliphatic diisocyanates used are customary aliphatic and / or cycloaliphatic diisocyanates, for example tri-, tetra-, penta-, hexa-, hepta- and / or octamethylene diisocyanate, 2-methylpentamethylene-1,5-diisocyanate, 2-ethyltetramethylene 1, 4-diisocyanate, hexamethylene-1,6-diisocyanate (HDI), pentamethylene-1,5-diisocyanate, butylene-1,4-diisocyanate, trimethylhexamethylene-1,6-diisocyanate, 1-isocyanato 3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 1, 4- and / or 1, 3-bis (isocyanatomethyl) cyclohexane (HXDI), 1, 4-cyclohe
• Preferred aliphatic polyisocyanates are hexamethylene-1,6-diisocyanate (HDI), 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane and 4,4'-, 2,4'- and / or 2,2 '- Methylenedicyclohexyl diisocyanate (H12MDI).
• HDI hexamethylene-1,6-diisocyanate
• H12MDI 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane
• H12MDI 2,2 '- Methylenedicyclohexyl diisocyanate
• Preferred aliphatic polyisocyanates are hexamethylene-1,6-diisocyanate (HDI), 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane and 4,4'-, 2,4'- and / or 2,2 '-
• the present invention relates to a thermoplastic polyurethane as described above, wherein the polyisocyanate composition used comprises at least one polyisocyanate selected from the group consisting of methylene diphenyl diisocyanate (MDI), hexamethylene 1,6-diisocyanate (HDI) and 4,4 '. , 2,4'- and 2,2'-methylenedicyclohexyl diisocyanate (H12MDI).
• MDI methylene diphenyl diisocyanate
• HDI hexamethylene 1,6-diisocyanate
• H12MDI 2,4'- and 2,2'-methylenedicyclohexyl diisocyanate
• Suitable aromatic diisocyanates are, in particular, 1,5-naphthylene diisocyanate (NDI), 2,4- and / or 2,6-toluene diisocyanate (TDI), 3,3'-dimethyl-4,4'-diisocyanato-diphenyl (TODI), p-phenylene diisocyanate (PDI), diphenylethane-4,4'-diisoyanate (EDI), diphenylmethane diisocyanate, 3,3'-dimethyl-diphenyl-diisocyanate, 1, 2-diphenylethane-diisocyanate and / or phenylene-diisocyanate.
• NDI 1,5-naphthylene diisocyanate
• TDI 2,4- and / or 2,6-toluene diisocyanate
• TODI 3,3'-dimethyl-4,4'-diisocyanato-
• Preferred examples of higher functional isocyanates are triisocyanates, e.g. B. triphenylmethane-4,4 ', 4 "-triisocyant, furthermore the cyanurates of the abovementioned diisocyanates, as well as the oligomers obtainable by partial reaction of diisocyanates with water, for example the bisurethe of the abovementioned diisocyanates, furthermore oligomers, which are obtainable by targeted reaction of semi-blocked diisocyanates with polyols which have on average more than two and preferably three or more hydroxyl groups.
• the polyisocyanate composition may also contain one or more solvents. Suitable solvents are known to the person skilled in the art. Suitable examples are non-reactive solvents such as ethyl acetate, methyl ethyl ketone and hydrocarbons.
• crosslinkers for example the above-mentioned higher-functional polyisocyanates or polyols, or also other higher-functional molecules having a plurality of isocyanate-reactive functional groups.
• the components (i) to (iii) are used in a ratio such that the molar ratio of the sum of the functionalities of the polyol composition used and chain extenders to the sum of the functionalities of the isocyanate composition used ranges from 1 to 0, 8 to 1 to 1, 3 is located.
• the ratio is preferably in the range from 1 to 0.9 to 1 to 1.2, more preferably in the range from 1 to 0.965 to 1 to 1:05, particularly preferably in the range from 1 to 0.98 to 1 to 1, 03 ,
• the present invention relates to a thermoplastic polyurethane as described above, wherein the molar ratio of the sum of the functionalities of the polyol composition used and chain extenders to the sum of the functionalities of the isocyanate composition used in the range of 1 to 0.8 to 1 to 1, 3 is located.
• the index is defined by the ratio of the total isocyanate groups used in the reaction of component (i) to the isocyanate-reactive groups, ie in particular the groups of components (ii) and (iii).
• an isocyanate group of component (i) has an active hydrogen atom.
• more isocyanate groups exist than isocyanate-reactive groups.
• the present invention relates to a thermoplastic polyurethane as described above, wherein the ratio in the reaction in the range of 965 to 1 100 is.
• additives can be added in the reaction of components (i) to (iii), for example catalysts or auxiliaries and additives.
• Additives and auxiliaries are known per se to the person skilled in the art. Combinations of several additives can also be used according to the invention.
• the term additive is understood in particular as meaning catalysts, auxiliaries and additives, in particular stabilizers, nucleating agents, fillers or crosslinkers. Suitable additives or additives are for example stabilizers, nucleating agents, fillers such as silicates or crosslinkers such as polyfunctional aluminosilicates.
• the present invention accordingly relates to a thermoplastic polyurethane as described above, wherein the thermoplastic polyurethane contains at least one additive.
• auxiliaries and additives may be mentioned, for example, surface-active substances, flame retardants, nucleating agents, oxidation stabilizers, antioxidants, lubricants and mold release aids, dyes and pigments, stabilizers, eg. As against hydrolysis, light, heat or discoloration, inorganic and / or organic fillers, reinforcing agents and plasticizers.
• Suitable auxiliaries and additives can be found, for example, in the Kunststoffhandbuch, Volume VII, published by Vieweg and Hochtlen, Carl Hanser Verlag, Kunststoff 1966 (S103-13).
• Suitable catalysts are also known in principle from the prior art.
• Suitable catalysts are, for example, organic metal compounds selected from the group consisting of tin, titanium, zirconium, hafnium, bismuth, zinc, aluminum and iron organyls, for example tin organyl compounds, preferably tin dialkyls such as dimethyltin or diethyltin, or tin organyl compounds of aliphatic carboxylic acids, preferably tin diacetate, tin dilaurate, dibutyltin diacetate, dibutyltin dilaurate, bismuth compounds such as bismuth-alkyl compounds or the like, or iron compounds, preferably iron (MI) acetylacetonate or the metal salts of the carboxylic acids such as Tin isooctoate, tin dioctoate, titanic acid ester or bismuth (III) neodecanoate.
• tin organyl compounds preferably tin dialkyls such as dimethyltin or dieth
• the catalysts are selected from tin compounds and bismuth compounds, more preferably tin alkyl compounds or bismuth-halo compounds. Particularly suitable are the tin isooctoate and bismuth neodecanoate.
• the catalysts are usually used in amounts of 0 to 2000 ppm, preferably 1 ppm to 1000 ppm, more preferably 2 ppm to 500 ppm, and most preferably from 5 ppm to 300 ppm.
• thermoplastic polyurethanes according to the invention can vary within wide ranges, depending on the application.
• the thermoplastic polyurethanes of the invention have, for example, a Shore hardness in the range of 60 A to 80 D, determined according to DIN 53505, preferably in the range of 80 A to 60 D, determined according to DIN 53505, more preferably in the range of 95 A to 58 D, determined according to DIN 53505.
• the present invention relates to a thermoplastic polyurethane as described above, wherein the thermoplastic polyurethane has a Shore hardness in the range of 60 A to 80 D, determined according to DIN 53505.
• the optical properties of the thermoplastic polyurethanes of the invention are also advantageous.
• thermoplastic polyurethanes are preferably translucent, more preferably transparent. This is advantageous for many applications.
• the present invention relates to a thermoplastic polyurethane as described above, wherein the thermoplastic polyurethane is translucent to transparent.
• the present invention also relates to a thermoplastic polyurethane as described above, wherein the thermoplastic polyurethane is opaque.
• the present invention also relates to a process for the preparation of a thermoplastic polyurethane comprising the reaction of components (i) to (iii):
• the present invention also relates to a process for producing a thermoplastic polyurethane, comprising reacting components (i) to (iii): (i) a polyisocyanate composition;
• thermoplastic polyurethane also relates to a process for the preparation of a thermoplastic polyurethane comprising the reaction of components (i) to (iii):
• polystyrene resin contains at least polytetrahydrofuran (PTHF) and the polyisocyanate composition contains at least methylene diphenyl diisocyanate (MDI).
• PTHF polytetrahydrofuran
• MDI methylene diphenyl diisocyanate
• reaction of components (i) to (iii) can in principle be carried out under known reaction conditions.
• the reaction can be carried out batchwise or else continuously, for example in a belt process or a reaction extrusion process. Suitable methods are described, for example, in EP 0 922 552 A1 or WO 2006/082183 A1
• reaction of components (i) to (iii) is carried out at elevated temperatures as room temperature.
• the heating can be carried out according to the invention in any suitable manner known to the person skilled in the art.
• the reaction is conducted in such a way that the zone temperature is in the range from 170 ° C. to 245 ° C., preferably in the range from 180 ° C. to 235 ° C., more preferably in the range from 190 ° C. up to 230 ° C.
• the present invention also relates to a process for producing a thermoplastic polyurethane as described above, wherein the reaction is carried out by a reaction extrusion method and the zone temperature is in the range of 170 ° C to 245 ° C.
• the method comprises further steps, for example a pretreatment of the components or an aftertreatment of the resulting thermoplastic polyurethane.
• the present invention also relates to a process for producing a thermoplastic polyurethane as described above, wherein after the reaction, the resulting thermoplastic polyurethane is tempered.
• the thermoplastic polyurethane according to the invention or a thermoplastic polyurethane obtained or obtainable by a process according to the invention can be used in many ways.
• the thermoplastic polyurethanes according to the invention are suitable for the production of molded parts and films, more preferably for the production of hoses.
• the present invention therefore also relates to the use of a thermoplastic polyurethane as described above or of a thermoplastic polyurethane obtainable or obtained by a process according to the invention for producing injection-molded products, Extruded products, films, and moldings.
• the present invention relates to the use as described above, wherein the shaped body is a hose.
• the high bursting pressure of the thermoplastic polyurethanes according to the invention is advantageous.
• the present invention also relates to the injection molding products, extruded products, films or moldings obtained by a method according to the invention, for example hoses cable sheathing or conveyor belts.
• a method according to the invention for example hoses cable sheathing or conveyor belts.
• the resulting injection-molded products, extruded products, films or moldings it is also possible for the resulting injection-molded products, extruded products, films or moldings to be subjected to an aftertreatment.
• the present invention relates to a tube comprising a thermoplastic polyurethane as described above or a thermoplastic polyurethane obtainable or obtained by a method as described above.
• the hose can have further components.
• the tube may be multi-layered and reinforced by conventional means. Suitable for reinforcement are, for example, fibers or fabrics, for example those made of glass, textiles or metals.
• the present invention accordingly relates to a hose as described above, wherein the hose is constructed in multiple layers.
• the present invention accordingly relates to a hose as described above, wherein the hose is reinforced by fibers or fabrics.
• the shaped body for example the film or the tube
• an aftertreatment for example crosslinking
• the present invention accordingly relates to a film or a tube as described above, wherein the film or the tube has been subjected to a post-treatment.
• thermoplastic polyurethane according to the invention can be used for pneumatic applications and after tempering at dimensions 5.8 * 8.2 mm with a Shore hardness of 98 A a bursting pressure at 70 ° C. greater than 20 bar.
• Other preferred applications are as Jardinummantellungen or for the production of conveyor belts.
• the high heat resistance of the thermoplastic polyurethanes according to the invention is advantageous for use as a cable sheath. In the context of the present invention, the heat resistance is determined by means of the TMA onset temperature.
• Thermoplastic polyurethane obtainable or obtained by reacting at least components (i) to (iii): a polyisocyanate composition;
• polystyrene resin contains at least polytetrahydrofuran (PTHF) and the polyisocyanate composition contains at least methylene diphenyl diisocyanate (MDI).
• PTHF polytetrahydrofuran
• MDI methylene diphenyl diisocyanate
• polystyrene contains at least one further polyol selected from the group consisting of polyethylene glycol, polypropylene glycol, polycarbonate (diol) and polycaprolactone.
• Thermoplastic polyurethane according to embodiment 1 or 2 wherein at least one further chain extender is used selected from the group consisting of compounds having at least two isocyanate-reactive functional groups.
• Thermoplastic polyurethane according to one of embodiments 1 to 3 wherein at least one further chain extender selected from the group consisting of noethylenglycol, aminopropanol, 1, 4-butanediol and hydroxyquinone (bis (2-hydroxyethyl)) ether (HQEE) is used.
• Thermoplastic polyurethane according to one of embodiments 1 to 4 wherein the molar ratio of the sum of the functionalities of the polyol composition used and chain extenders to the sum of the functionalities of the isocyanate composition used in the range of 1 to 0.8 to 1 to 1.3.
• thermoplastic polyurethane according to any one of embodiments 1 to 6, wherein the polytetrahydrofuran has a molecular weight Mn in the range of 650 g / mol to 1400 g / mol.
• thermoplastic polyurethane according to any of embodiments 1 to 10 or a thermoplastic polyurethane obtainable or obtained by a process according to embodiment 1 1 for the production of injection molded products, extrusion ons coinciden, films and moldings.
• hose comprising a thermoplastic polyurethane according to any of embodiments 1 to 10 or a thermoplastic polyurethane obtainable or obtained by a process according to embodiment 11. 15. Hose according to embodiment 14, wherein the hose is constructed in multiple layers.
• thermoplastic polyurethane obtainable or obtained by reacting at least components (i) to (iii):
• MDI methylene diphenyl diisocyanate
• Thermoplastic polyurethane according to any one of embodiments 18 to 21, wherein the polyisocyanate composition used comprises at least one polyisocyanate selected from the group consisting of methylenediphenyl diisocyanate (MDI), hexamethylene-1,6-diisocyanate (HDI) and 4,4'-, 2,4'- and 2,2'-methylenedicyclohexyl diisocyanate (H12MDI).
• MDI methylenediphenyl diisocyanate
• HDI hexamethylene-1,6-diisocyanate
• H12MDI 4,4'-, 2,4'- and 2,2'-methylenedicyclohexyl diisocyanate
• thermoplastic polyurethane according to any one of embodiments 18 to 25, wherein the thermoplastic polyurethane has a Shore hardness in the range of 60 A to 80 D, determined according to DIN 53505.
• thermoplastic polyurethane according to any of embodiments 18 to 26 wherein the thermoplastic polyurethane is translucent to transparent , Thermoplastic polyurethane according to any one of embodiments 18 to 26, wherein the thermoplastic polyurethane is opaque.
• thermoplastic polyurethane a polyol composition, wherein in addition to 1, 3-propanediol no further chain extender is used.
• a thermoplastic polyurethane according to any of embodiments 18 to 29 or a thermoplastic polyurethane obtainable or obtained by a process according to embodiment 30 for the production of injection molded products, extrusion ons occur, films and moldings.
• Thermoplastic polyurethane obtainable or obtained by reacting at least components (i) to (iii): a polyisocyanate composition;
• Thermoplastic polyurethane according to embodiment 32 obtainable or obtained by reacting at least components (i) to (iii): a polyisocyanate composition;
• thermoplastic polyurethane according to embodiment 32 or 33 wherein the polyol composition used is free of polytetrahydrofuran (PTHF) and in the implementation of no polytetrahydrofuran (PTHF) is used as a further component.
• PTHF polytetrahydrofuran
• PTHF polytetrahydrofuran
• PTHF polytetrahydrofuran
• DI methylene diphenyl diisocyanate
• MDI methylene diphenyl diisocyanate
• thermoplastic polyurethane according to any one of embodiments 32 to 35, wherein the polyol composition used contains at least one polyol selected from the group consisting of polyethylene glycol, polypropylene glycol, polyadipates, polycarbonate (diols) and polycaprolactones. 37. Thermoplastic polyurethane according to embodiment 32 obtainable or obtained by reacting at least components (i) to (iii):
• polystyrene resin contains at least polytetrahydrofuran (PTHF) and the polyisocyanate composition contains at least methylene diphenyl diisocyanate (MDI).
• PTHF polytetrahydrofuran
• MDI methylene diphenyl diisocyanate
• thermoplastic polyurethane according to embodiment 37 wherein the polyol composition contains at least one further polyol selected from the group consisting of polyethylene glycol, polypropylene glycol, polycarbonate (diol) and polycaprolactone.
• 39. Thermoplastic polyurethane according to embodiment 37 or 38, wherein in addition to 1, 3-propanediol no further chain extender is used.
• 40. Thermoplastic polyurethane according to embodiment 37 or 38, wherein at least one further chain extender is used selected from the group consisting of compounds having at least two isocyanate-reactive functional groups.
• Thermoplastic polyurethane according to embodiment 40 wherein at least one further chain extender selected from the group consisting of monoethylene glycol, aminopropanol, 1, 4-butanediol, 1, 6-hexanediol and hydroxyquinone (bis (2-hydroxyethyl)) ether (HQEE) is used.
• at least one further chain extender selected from the group consisting of monoethylene glycol, aminopropanol, 1, 4-butanediol, 1, 6-hexanediol and hydroxyquinone (bis (2-hydroxyethyl)) ether (HQEE) is used.
• thermoplastic polyurethane according to any one of embodiments 37 to 41, wherein the polytetrahydrofuran has a molecular weight Mn in the range of 650 g / mol to 1400 g / mol.
• Thermoplastic polyurethane according to any of embodiments 32 to 42, wherein the polyisocyanate composition used comprises at least one polyisocyanate selected from the group consisting of methylenediphenyl diisocyanate (MDI), hexamethylene-1,6-diisocyanate (HDI) and 4,4'-, 2,4'- and 2,2'-methylenedicyclohexyl diisocyanate (H12MDI).
• MDI methylenediphenyl diisocyanate
• HDI hexamethylene-1,6-diisocyanate
• H12MDI 4,4'-, 2,4'- and 2,2'-methylenedicyclohexyl diisocyanate
• thermoplastic polyurethane according to any one of embodiments 32 to 44, wherein the ratio in the reaction is in the range of 965 to 1100.
• thermoplastic polyurethane according to any one of embodiments 32 to 46, wherein the thermoplastic polyurethane has a Shore hardness in the range of 60 A to 80 D, determined according to DIN 53505.
• thermoplastic polyurethane according to any one of embodiments 32 to 47, wherein the thermoplastic polyurethane is translucent to transparent.
• thermoplastic polyurethane according to any one of Embodiments 32 to 47, wherein the thermoplastic polyurethane is opaque.
• thermoplastic polyurethane according to Embodiment 51, which comprises reacting components (i) to (iii):
• thermoplastic polyurethane a polyol composition, wherein in addition to 1, 3-propanediol no further chain extender is used.
• a process for producing a thermoplastic polyurethane according to Embodiment 51 which comprises reacting components (i) to (iii):
• thermoplastic polyurethane according to one of the embodiments 32 to 50 or of a thermoplastic polyurethane obtainable or obtained by a process according to one of the embodiments 51 to 53 for the production of injection molded products, extruded products, films and moldings.
• a thermoplastic polyurethane according to one of the embodiments 32 to 50 or of a thermoplastic polyurethane obtainable or obtained by a process according to one of the embodiments 51 to 53 for the production of injection molded products, extruded products, films and moldings.
• the shaped body is a hose.
• a tube comprising a thermoplastic polyurethane according to any of embodiments 31 to 48 or a thermoplastic polyurethane obtainable or obtained by a method according to any one of embodiments 51 to 53.
• Hose according to embodiment 56 wherein the hose is constructed in multiple layers.
• Hose according to embodiment 56 or 57 wherein the hose is reinforced by fibers or fabrics.
• Polyol 1 Polyether polyol with an OH number of 1 12.2 and excluding primary OH groups (based on tetramethylene oxide, functionality: 2)
• Isocyanate 1 aromatic isocyanate (4,4'-methylene diphenyl diisocyanate) KV 1: 1, 3-propanediol KV 2: 1, 4-butanediol
• Catalyst 1 Tin isooctoate (50% in dioctyl adipate)
• Stabilizer 1 Sterically hindered phenol
• thermoplastic polyurethane (TPU) was synthesized from 4,4'-diphenylmethane diisocyanate, chain extender 1, 3-propanediol, phenolic antioxidant, and polytetrahydrofuran having a number average molecular weight of 1 kg / mol with stirring in a reaction vessel.
• the starting temperature was 80 ° C.
• the solution was poured onto a heated to 125 ° C hot plate and the resulting TPU plate granulated after annealing.
• the measured values were produced by injection molding plates or tubes, wherein the zone temperatures of the extruders used were between 190 ° C and 235 ° C.
• the synthesis and properties of thermoplastic polyurethanes obtained are summarized in Tables 1 and 2.
• Example 3 At a starting temperature of 60 ° C, when a temperature of 80 ° C is reached, the mixture is poured onto a heated to 80 ° C hotplate.
• the products prepared using 1,4-butanediol as chain extenders serve as comparative examples.
• Example 1 Example 2 Example 3 Example 4
• a mixture of chain extender 1, 3-propanediol, a phenolic antioxidant, and polytetrahydrofuran having a number average molecular weight of 1 kg / mol was heated to 70 ° C and mixed thoroughly in a mixing head with 4,4'-diphenylmethane diisocyanate.
• the resulting reaction mixture was applied to a circulating PTFE tape at a temperature of 90 ° C.
• the solidified at the end of the tape to a solid band (rind) reaction mixture was fed at about 80 ° C via feed rollers continuously directly to a crushing and homogenizing. There it was crushed at temperatures of about 105 ° C and conveyed into a tangential flanged single-screw extruder.
• the housing temperatures were in the catchment area at about 170 ° C to 190 ° C, in the central zone at 210 to 230 ° C.
• the melt emerging from the nozzle plate was made into uniform lentil granules using underwater granulation and then dried.
• the temperature setting values of the housings were 200 ° C downstream in the first worm third, 170 ° C in the second worm third, and 190 ° C in the third and last wrench thirds.
• the output was 850 kg / h.
• the granules were then further processed by injection molding into test specimens or by extrusion to form hoses.
• the tubing was extruded on a 45 gauge Arenz extruder with 3-zone screw with 9.8 mm die and a 6.9 mm mandrel.
• the zone temperatures were between 180 and 225 ° C.
• the hose geometry was adjusted by varying the take-off speed and pressure in a water bath with vacuum calibration.
• thermoplastic polyurethanes prepared by continuous synthesis are summarized in Table 3 and Table 4.
• Table 3 Examples of synthesis:
• the TMA Onset temperature given in Table 4 serves as a measure of the heat resistance.
• the TMA was measured at a heating rate of 20 ° C / min.
• the onset temperature was specified.
• Polyol 1 Polyether polyol with an OH number of 1 12.2 and excluding primary OH groups (based on tetramethylene oxide, functionality: 2)
• Polyol 2 Polyester polyol with an OH number of 56 and excluding primary
• Isocyanate 1 aromatic isocyanate (4,4'-methylene diphenyl diisocyanate)
• Catalyst 1 stannous isooctoate (50% in dioctyl adipate)
• Stabilizer 1 Sterically hindered phenol
• the products prepared using 1,4-butanediol as chain extender serve as comparative examples.
• the creep behavior was determined by stretching a tempered (20 h / 100 ° C) S1 tensile bar by 5%. The force or tension that occurs for the first time at this stretch is maintained at room temperature for 12 hours. After relaxation, the length difference determined. The given values reflect dispersion at the carried-out repetitions of measurement.
• Polyester polyol with an OH number of 56 and excluding primary OH groups (based on adipic acid, butanediol and monoethylglycol, functionality: 2)
• Polyester polyol with an OH number of 52 and excluding primary OH groups (based on adipic acid and monoethylene glycol, functionality: 2)
• Catalyst 2 tin isooctoate (50% in dioctyl adipate)
• Stabilizer 2 Sterically hindered phenol
• thermoplastic polyurethane (TPU) was synthesized from 4,4'-diphenylmethane diisocyanate, chain extender 1, 3-propanediol, phenolic antioxidant, and a polyadipic acid ester diol having an OH number of 56 with stirring in a reaction vessel. After reaching a reaction temperature of 1 10 ° C, the solution was poured onto a temperature-controlled hot plate and the resulting TPU plate granulated after annealing. The measured values were produced by injection molding plates or tubes, wherein the zone temperatures of the extruders used were between 190 ° C and 235 ° C.
• thermoplastic polyurethanes obtained are summarized in Table 7 and 8.
• Table 7 Examples of synthesis:
• a mixture of chain extender 1, 3-propanediol, a phenolic antioxidant, and a polyadipic ester diol having an OH number of 56 was heated to 80 ° C and mixed thoroughly in a mixing head with 4,4'-diphenylmethane diisocyanate.
• the resulting reaction mixture was applied to a circulating PTFE tape at a temperature of 95 ° C.
• the reaction mixture solidified at the end of the strip into a solid strip (rind), was fed continuously at approximately 80 ° C. via draw-in rollers directly to a comminuting and homogenizing device. There it was crushed at temperatures of about 105 ° C and conveyed into a tangential flanged single-screw extruder.
• the housing temperatures were in the catchment area at about 170 ° C to 190 ° C, in the central zone at 190 to 220 ° C.
• the melt leaving the nozzle plate was made into uniform lenticular granules using underwater granulation and then dried.
• the temperature setting values of the housings were 200 ° C downstream in the first worm third, 170 ° C in the second worm third, and 190 ° C in the third and last wrench thirds.
• the output was 850 kg / h.
• the granules were then further processed by injection molding into test specimens or by extrusion to form hoses.
• the tubing was extruded on a 45 gauge Arenz extruder with 3-zone screw with 9.8 mm die and a 6.9 mm mandrel.
• the zone temperatures were between 180 and 225 ° C.
• the hose geometry was adjusted by varying the take-off speed and pressure in a water bath with vacuum calibration.
• thermoplastic polyurethanes prepared by continuous synthesis are summarized in Table 9 and Table 10.
• Polyol 2 [g] 1000 1000 1000 1000 1000 1000

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