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WO2025168329A1 - Procédé de préparation de polyuréthanes thermoplastiques contenant de l'éther de polypropylène - Google Patents

Procédé de préparation de polyuréthanes thermoplastiques contenant de l'éther de polypropylène

Info

Publication number
WO2025168329A1
WO2025168329A1 PCT/EP2025/051407 EP2025051407W WO2025168329A1 WO 2025168329 A1 WO2025168329 A1 WO 2025168329A1 EP 2025051407 W EP2025051407 W EP 2025051407W WO 2025168329 A1 WO2025168329 A1 WO 2025168329A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
diisocyanate
mixture
articles
mixtures
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.)
Pending
Application number
PCT/EP2025/051407
Other languages
German (de)
English (en)
Inventor
Yi SHEN
Franz-Heinrich HERMANNS
Michael Kessler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Original Assignee
Covestro Deutschland AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Covestro Deutschland AG filed Critical Covestro Deutschland AG
Publication of WO2025168329A1 publication Critical patent/WO2025168329A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/281—Monocarboxylic acid compounds
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4808—Mixtures of two or more polyetherdiols
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group

Definitions

  • the present invention relates to a process for producing polypropylene ether-containing thermoplastic polyurethanes, as well as to polypropylene ether-containing thermoplastic polyurethanes obtained or obtainable by these processes. Furthermore, the invention relates to the use of these polypropylene ether-containing thermoplastic polyurethanes and to articles comprising or consisting of the polypropylene ether-containing thermoplastic polyurethane.
  • TPUs Thermoplastic polyurethanes
  • TPUs are composed of linear polyols, usually polyethers or polyesters, organic diisocyanates, and short-chain diols (chain extenders).
  • TPUs are usually solvent-free and can be produced continuously or batchwise.
  • the best known technical manufacturing processes which are also used technically, are the belt process (GB 1057018 A) and the extruder process (DE 1964834 A-l and DE 2059570 A-l).
  • the components can be varied within a relatively wide molar ratio.
  • Molar ratios of macrodiols to chain extenders ranging from 1:1 to 1:12 have proven effective.
  • the amount of chain extender allows the hardness of the TPU to be adjusted within a wide range. This results in products with hardnesses ranging from approximately 40 Shore A to approximately 85 Shore D.
  • TPUs that exhibit a very high solidification rate after processing in injection-molded articles are of particular interest across the entire hardness range from approximately 40 Shore A to approximately 85 Shore D.
  • the full potential of the mechanical properties and processing characteristics cannot often be fully exploited.
  • a process for producing thermoplastically processable polyurethanes is described by W. B syndromeer et al. (EP-A 1757632).
  • a multi-stage OH prepolymer process improves the homogeneity of the TPU. However, this improved homogeneity slows the solidification rate of the TPU.
  • polypropylene glycol or poly(propylene oxide) homopolymers (hereinafter also referred to as C3 polyether homopolymer polyol) as a polyol component in the production of thermoplastic polyurethanes is interesting, among other things, due to its low cost.
  • polypropylene glycol in the production of thermoplastic polyurethanes is known, for example, from WO 2020/109566 A1, in which polyols based on polypropylene glycol are reacted with polyisocyanates.
  • the invention relates to the use of the thermoplastic polyurethane according to the invention for the production of injection-molded articles, extruded articles, pressed articles, compression-molded articles, 3D-printed articles, articles for mechanical engineering, road and rail construction, medical and dental articles, in particular splints for the treatment of malocclusions, shoes, in particular ski boots, articles for the automotive industry, articles for the electrical industry, in particular cable sheathing, housings and plugs, consumer articles, coatings, hoses, profiles, belts, films, fibers, nonwovens, textiles, damping elements, sealing materials.
  • C2 polyether homopolymer polyol is defined as a polyol based on polyethylene glycol or poly(ethylene oxide)
  • C3 polyether homopolymer polyol is defined as a polyol based on Based on polypropylene glycol or poly(propylene oxide)
  • C2/C3 polyether block copolymer polyol is understood to mean a polyol based on polyethylene glycol or poly(ethylene oxide) as well as polypropylene glycol or poly(propylene oxide).
  • the "C” in "C2,”"C3,” etc., stands for a carbon atom, with the number following it indicating the number of carbon atoms in the repeating unit of the respective polymer.
  • the mass ratio of component (Al) to (A2) is > 1:9, preferably > 3:7, in each case based on the total mass of components (Al) and (A2).
  • component (A) consists exclusively of component (Al).
  • Suitable organic polyisocyanates of component (B) used in steps 1) and 3) include, for example, aliphatic, cycloaliphatic, araliphatic, heterocyclic and aromatic polyisocyanates, as described in Justus Liebigs Annalen der Chemie, 562, pp. 75-136.
  • aliphatic diisocyanates such as 1,6-hexamethylene diisocyanate
  • cycloaliphatic diisocyanates such as isophorone diisocyanate, 1,4-cyclohexane diisocyanate, 1-methyl-2,4-cyclohexane diisocyanate and 1-methyl-2,6-cyclohexane diisocyanate and the corresponding isomer mixtures
  • 4,4'-dicyclohexylmethane diisocyanate 2,4'-dicyclohexylmethane diisocyanate and 2,2'-dicyclohexylmethane diisocyanate and the corresponding isomer mixtures
  • aromatic diisocyanates such as 2,4-tolylene diisocyanate, mixtures of 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,4'-dipheny
  • Suitable as component (C) are all linear diols known to the skilled person with a molecular weight of 62 g/mol to 500 g/mol.
  • the diols and/or their precursor compounds can be obtained from fossil or biological sources.
  • Suitable diols are preferably aliphatic diols having 2 to 14 carbon atoms, such as ethanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, diethylene glycol, and dipropylene glycol.
  • diesters of terephthalic acid with glycols containing 2 to 4 carbon atoms such as terephthalic acid bis-ethylene glycol or terephthalic acid bis-1,4-butanediol, hydroxyalkylene ethers of hydroquinone, such as 1,4-di-(hydroxyethyl)-hydroquinone, and ethoxylated bisphenols, are also suitable.
  • Particularly preferred short-chain diols are ethanediol, 1,4-butanediol, 1,6-hexanediol, and 1,4-di-(hydroxyethyl)-hydroquinone.
  • Mixtures of the aforementioned chain extenders can also be used. Small amounts of diamines and/or triamines can also be added.
  • one or more diols selected from the group consisting of 1,2-ethanediol, 1,4-butanediol, 1,6-hexanediol, 1,4-di-(beta-hydroxyethyl)hydroquinone or a mixture of at least two of these are used as component (C), preferably 1,2-ethanediol, 1,4-butanediol or mixtures thereof are used as component (C) and particularly preferably 1,4-butanediol is used as component (C).
  • Phosphoric acid, p-toluenesulfonic acid monohydrate and adipic acid can be used as non-oxidizing acids (D).
  • catalysts commonly used in polyurethane chemistry can be used as catalysts (E).
  • Suitable catalysts are known and common tertiary amines, such as E.g., triethylamine, dimethylcyclohexylamine, N-methylmorpholine, N,N'-dimethylpiperazine, 2-(dimethylaminoethoxy)ethanol, diazabicyclo[2,2,2]octane, and the like, as well as, in particular, organic metal compounds such as titanic acid esters, iron compounds, bismuth compounds, tin compounds, e.g., tin diacetate, tin dioctoate, tin dilaurate, or the tin dialkyl salts of aliphatic carboxylic acids such as dibutyltin diacetate, dibutyltin dilaurate, or the like.
  • Preferred catalysts are organic metal compounds, in particular titanic acid esters, iron or tin compounds. Dibuty
  • Additives, auxiliaries, and additives (F) that can be used include, for example, lubricants such as fatty acid esters, their metal soaps, fatty acid amides, and silicone compounds, antiblocking agents, inhibitors, stabilizers against hydrolysis, light, heat, and discoloration, flame retardants, dyes, pigments, inorganic or organic fillers, nucleating agents, and reinforcing agents.
  • Reinforcing agents are, in particular, fibrous reinforcing materials such as inorganic fibers, which are manufactured using state-of-the-art technology and may also be coated with a size. Further information on the aforementioned auxiliaries and additives can be found in the specialist literature, for example, J.H. Saunders, K.C.
  • Monoalcohols such as 1-butanol, 1-hexanol, 1-octanol and stearyl alcohol or monoamines such as 1-butylamine and stearylamine can be used as monofunctional chain terminators (G) to adjust a specific TPU molecular weight.
  • the pH values are determined electrochemically at 23°C in accordance with DIN 19268:2021-10.
  • the measurement is performed using the pH electrode "Solvotrode Easy Clean 6.0229.010" from Methrom AG.
  • the Solvotrode is supplied with 2 mol/L LiCl in ethanol as the reference electrolyte.
  • the theoretical hardness of the thermoplastic obtained according to the invention is the thermoplastic obtained according to the invention.
  • the Charpy impact strength measured at -20 °C according to DIN EN ISO 179/11A (2010) is understood in this invention as a measure of low-temperature impact strength.
  • the injection-molded parts undergo Charpy impact strength testing according to DIN EN ISO 179/11A (2010) at -20 °C.
  • the test specimen has the following dimensions: 80 ⁇ 2 mm length, 10.0 ⁇ 0.2 mm width, and 4.0 ⁇ 0.2 mm thickness.
  • the test specimen is notched.
  • the notch root radius rN is 0.25 ⁇ 0.05 mm.
  • Polyol 2 poly(propylene oxide)-poly(ethylene oxide) block copolymer (C2/C3 polyether block copolymer polyol): propylene glycol (starter) with polymerized alkylene oxides (molar ratio of ethylene oxide units to propylene oxide units of approximately 51:49); OH number approximately 56, proportion of primary terminal OH groups: >90%), KOH catalyzed
  • Step 1 Partial amount 1 (see Table 1) of the MDI is brought to a conversion of > 90 mol-%, based on the polyol, at approx. 140°C with 1 mol of polyol or polyol mixture while stirring.
  • Step 2 The chain extender is added to the stirred reaction mixture and stirred vigorously for approximately 10 seconds. The acid is then added in defined amounts (Table 1).
  • the resulting TPU cast sheets were cut and granulated.
  • the granules were processed into rods (mold temperature: 40°C; rod size: 80x10x4 mm) or sheets (mold temperature: 70°C; size: 125x50x2 mm) using an Arburg Allrounder 470S injection molding machine at a temperature range of 180°C to 230°C and a pressure range of 650 to 750 bar with an injection flow rate of 10 to 35 cm3/s.
  • the TPU can also be produced continuously, e.g. using a twin-screw reaction extruder (however, the production is not limited to this form of presentation, see “belt process”).
  • the MDI portion 1, preheated to 60°C was metered into a tube equipped with a spiked mixer.
  • a polyol or polyol mixture heated to 140°C was pumped into the same tube.
  • the tube had a length/diameter ratio of 8:1.
  • the reaction mixture flowed continuously into a connected twin-screw extruder, which was heated externally to 140°C to 220°C.
  • the acid was metered into the chain extender, and the chain extender and portion 2 of the MDI were added in the middle of the screw.
  • the screw shaft speed was 300 rpm.
  • the hot melt was granulated and cooled.
  • the granules were Injection molded into test specimens on which the properties listed in the table were measured.
  • Comparative Examples 1 and 2 are TPU formulations without added acid. Comparative Example 1 has a very low tensile strength. With increased theoretical hardness (Comparative Example 2), TPU cannot be produced and/or processed by injection molding.
  • Examples 3, 10, 11, and 12 show TPU formulations with increased theoretical hardness with the addition of the acids, with good tensile strength and good low-temperature impact strength (Charpy impact strength).
  • the Charpy impact strength is comparable to TPUs based on C4 polyether homopolymer polyols.
  • the use of C3 polyether homopolymer polyols is more cost-effective and has a better CCU balance than C4 polyether homopolymer polyols.

Landscapes

  • 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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un procédé de préparation de polyuréthanes thermoplastiques contenant de l'éther de polypropylène et des polyuréthanes thermoplastiques contenant de l'éther de polypropylène obtenus ou pouvant être obtenus selon ces procédés. L'invention concerne en outre l'utilisation de ces polyuréthanes thermoplastiques contenant de l'éther de polypropylène et des articles comprenant du polyuréthane thermoplastique contenant de l'éther de polypropylène ou constitués dudit polyuréthane.
PCT/EP2025/051407 2024-02-09 2025-01-21 Procédé de préparation de polyuréthanes thermoplastiques contenant de l'éther de polypropylène Pending WO2025168329A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP24156794 2024-02-09
EP24156794.0 2024-02-09

Publications (1)

Publication Number Publication Date
WO2025168329A1 true WO2025168329A1 (fr) 2025-08-14

Family

ID=89900657

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2025/051407 Pending WO2025168329A1 (fr) 2024-02-09 2025-01-21 Procédé de préparation de polyuréthanes thermoplastiques contenant de l'éther de polypropylène

Country Status (1)

Country Link
WO (1) WO2025168329A1 (fr)

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59570C (de) Firma ERFURTH & SlNELL in Berlin S.W., Neuenburgerstrafse 7 Elektrische Stromzuführung für Stromschlufswagen und Stromweichen
GB1057018A (en) 1964-12-14 1967-02-01 Ici Ltd Polyurethane polymers
DE2059570A1 (de) 1969-12-03 1971-06-09 Upjohn Co Kontinuierliches Einschritt-Herstellungsverfahren fuer ein thermoplastisches,unporiges Polyurethan
DE1964834A1 (de) 1969-12-24 1971-07-01 Bayer Ag Verfahren zur Herstellung von Polyurethan-Elastomeren
US3996172A (en) * 1973-06-04 1976-12-07 The Dow Chemical Company Non-elastomeric polyurethane compositions
DE2901774A1 (de) 1979-01-18 1980-07-24 Elastogran Gmbh Rieselfaehiges, mikrobenbestaendiges farbstoff- und/oder hilfsmittelkonzentrat auf basis eines polyurethan-elastomeren und verfahren zu seiner herstellung
US4980445A (en) 1989-01-17 1990-12-25 The Dow Chemical Company Thermoplastic polyurethanes
US5128087A (en) * 1990-03-09 1992-07-07 Miles Inc. Process for the production of molded products using internal mold release agents
US5795948A (en) 1992-05-26 1998-08-18 Bayer Aktiengesellschaft Multistage process for production of thermoplastic polyurethane elastomers
EP1338614A1 (fr) 2002-02-23 2003-08-27 Bayer Ag Procédé de production des elastomères de polyuréthane thermoplastiques, mous, facilement démoulables et à retrait minime
EP1757632A2 (fr) 2005-08-24 2007-02-28 Bayer MaterialScience AG Procédé pour produire de polyuréthanes thermoplastiques
WO2018158327A1 (fr) 2017-03-02 2018-09-07 Covestro Deutschland Ag Polyuréthannes thermoplastiques résistants au choc, leur production et leur utilisation
WO2020109566A1 (fr) 2018-11-29 2020-06-04 Basf Se Préparation en continu d'un tpus à base de ppg
EP3812408A1 (fr) * 2019-10-23 2021-04-28 Covestro Deutschland AG Polymère de polyuréthane présentant une dureté <= 60 shore a et une bonne résistance à l'abrasion

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59570C (de) Firma ERFURTH & SlNELL in Berlin S.W., Neuenburgerstrafse 7 Elektrische Stromzuführung für Stromschlufswagen und Stromweichen
GB1057018A (en) 1964-12-14 1967-02-01 Ici Ltd Polyurethane polymers
DE2059570A1 (de) 1969-12-03 1971-06-09 Upjohn Co Kontinuierliches Einschritt-Herstellungsverfahren fuer ein thermoplastisches,unporiges Polyurethan
DE1964834A1 (de) 1969-12-24 1971-07-01 Bayer Ag Verfahren zur Herstellung von Polyurethan-Elastomeren
US3996172A (en) * 1973-06-04 1976-12-07 The Dow Chemical Company Non-elastomeric polyurethane compositions
DE2901774A1 (de) 1979-01-18 1980-07-24 Elastogran Gmbh Rieselfaehiges, mikrobenbestaendiges farbstoff- und/oder hilfsmittelkonzentrat auf basis eines polyurethan-elastomeren und verfahren zu seiner herstellung
US4980445A (en) 1989-01-17 1990-12-25 The Dow Chemical Company Thermoplastic polyurethanes
US5128087A (en) * 1990-03-09 1992-07-07 Miles Inc. Process for the production of molded products using internal mold release agents
US5795948A (en) 1992-05-26 1998-08-18 Bayer Aktiengesellschaft Multistage process for production of thermoplastic polyurethane elastomers
EP1338614A1 (fr) 2002-02-23 2003-08-27 Bayer Ag Procédé de production des elastomères de polyuréthane thermoplastiques, mous, facilement démoulables et à retrait minime
EP1757632A2 (fr) 2005-08-24 2007-02-28 Bayer MaterialScience AG Procédé pour produire de polyuréthanes thermoplastiques
WO2018158327A1 (fr) 2017-03-02 2018-09-07 Covestro Deutschland Ag Polyuréthannes thermoplastiques résistants au choc, leur production et leur utilisation
WO2020109566A1 (fr) 2018-11-29 2020-06-04 Basf Se Préparation en continu d'un tpus à base de ppg
EP3812408A1 (fr) * 2019-10-23 2021-04-28 Covestro Deutschland AG Polymère de polyuréthane présentant une dureté <= 60 shore a et une bonne résistance à l'abrasion

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
"Taschenbuch der Kunststoff-Additive", 1989, HANSER VERLAG
J.H. SAUNDERSK.C. FRISCH: "High Polymers", 1962, INTERSCIENCE PUBLISHERS
JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 562, pages 75 - 136
KUNSTSTOFFE, vol. 35, 1982, pages 568 - 584
KUNSTSTOFFE, vol. 68, 1978, pages 819 - 825

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