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EP4010390A1 - Procédé de production de polymères de polyuréthane pouvant être traités thermoplastiquement - Google Patents

Procédé de production de polymères de polyuréthane pouvant être traités thermoplastiquement

Info

Publication number
EP4010390A1
EP4010390A1 EP20751142.9A EP20751142A EP4010390A1 EP 4010390 A1 EP4010390 A1 EP 4010390A1 EP 20751142 A EP20751142 A EP 20751142A EP 4010390 A1 EP4010390 A1 EP 4010390A1
Authority
EP
European Patent Office
Prior art keywords
component
mol
range
shore
thermoplastically processable
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
EP20751142.9A
Other languages
German (de)
English (en)
Inventor
Yi SHEN
Franz-Heinrich HERMANNS
Christian Wamprecht
Peter Reichert
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 Intellectual Property GmbH and Co KG
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 Intellectual Property GmbH and Co KG filed Critical Covestro Intellectual Property GmbH and Co KG
Publication of EP4010390A1 publication Critical patent/EP4010390A1/fr
Pending legal-status Critical Current

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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • 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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • 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
    • C08G18/4825—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
    • C08G18/28—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
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5036—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/5045—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing urethane 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
    • C08G18/724—Combination of aromatic polyisocyanates with (cyclo)aliphatic polyisocyanates
    • 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
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • 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

  • TPU Thermoplastically processable polyurethane polymers
  • TPUs are of particular interest over the entire hardness range from approx. 40 Shore A to approx. 85 Shore D, which in the case of injection molded articles have a very high rate of solidification after the processing operation.
  • problems often arise with the chemical coupling of hard and soft segments due to excessive polarity differences between these phases.
  • the full potential of the mechanical properties and the processing properties can often not be fully exploited. There has been no lack of attempts to remedy these disadvantages by means of special processes.
  • this process has significant disadvantages, because the hard and soft phases are incompatible and thus a good coupling of this phase can no longer take place. As a result, the high molecular weight of the TPU that is necessary for good mechanical properties is not achieved. In practice, this process is also very unstable due to excessively high and fluctuating viscosities in the prepolymer stage and no longer functions satisfactorily below 60 Shore A, so that extruder standstills often occur.
  • the solvent-free process according to the invention can be carried out both by means of the hand-casting process and in a reactive extruder at temperatures of 160 to 240 ° C., preferably 170 to 240 ° C. and particularly preferably at 180 to 240 ° C.
  • linear polyols are particularly suitable as component (A): a) polyester polyols, b) polyether polyols, c) polyether esters, d) polycarbonate polyols, e) polyether carbonates, or any mixtures of polyols a) to e).
  • the molecular weights Mn of such polyols are usually calculated using their OH number (hydroxyl number), which is known to the person skilled in the art. The OH number is determined titrimetrically in accordance with DIN 53240.
  • the molecular weight of polyols can be calculated from the OH number (OHN) using the following formula:
  • Possible starter molecules are, for example: water, Amino alcohols, such as N-alkyl-diethanolamines, for example N-methyl-diethanol-amine, and diols, such as ethylene glycol, 1,3-propylene glycol, 1,4-butanediol and 1,6-hexanediol. If appropriate, mixtures of starter molecules can also be used.
  • Suitable polyether diols are also the hydroxyl-containing polymerization products of tetrahydrofuran. Trifunctional polyethers can also be used in proportions of 0 to 30% by weight, based on the bifunctional polyethers, but at most in such an amount that a thermoplastically processable product is formed.
  • the diisocyanates mentioned can be used individually or in the form of mixtures with one another.
  • diesters of terephthalic acid with glycols having 2 to 4 carbon atoms such as, for example, terephthalic acid-bis-ethylene glycol or terephthalic acid-bis-1,4-butanediol, hydroxyalkylene ethers of hydroquinone, such as 1,4-di- (hydroxyethyl) -hydroquinone, are also suitable and ethoxylated bisphenols.
  • Ethanediol, 1,4-butanediol, 1,6-hexanediol and 1,4-di (hydroxyethyl) hydroquinone are particularly preferably used as short-chain diols. Mixtures of the aforementioned chain extenders can also be used. Small amounts of diamines and / or triplets can also be added.
  • thermoplastically processable polyurethane polymer has a hardness greater than 70 Shore D, preferably in the range from 70 Shore D to 95 Shore D, particularly preferably in the range from 75 Shore D to 90 Shore D, in each case determined according to DIN ISO 7619-1 (2012-02-01).
  • the invention further provides a thermoplastically processable polyurethane polymer obtainable or obtained by the process according to the invention.
  • the polyurethane polymers produced by the process according to the invention have better properties than those produced by processes known from the prior art.
  • the polyurethane polymers according to the invention cure more quickly and have a higher Shore hardness and improved tensile strength.
  • the TPU sample is dissolved while stirring at room temperature in a 0.4% solution in N-methylpyrrolidone + 0.1% dibutylamine.
  • a so-called blank sample consisting of N-methylpyrrolidone and 0.1% dibutylamine solution, but without the TPU, is prepared.
  • the solutions are left to stand overnight and measured the next day.
  • the solutions are briefly stirred up again and then measured at 25 ° C using the SVM3000 / G2 Stabinger viscometer. The kinematic viscosity of the blank value and the solutions is measured.
  • Used raw materials :
  • Polyol 1 Desmophen ® 2028 (commercial product from Covestro Deutschland AG, polyester, molecular weight Mn approx. 2000 g / mol)
  • Stage 1 The partial amount 1 of the MDI is brought to a conversion of> 90 mol%, based on the polyol, at about 140 ° C with 1 mol polyol or polyol mixture while stirring.
  • Experiments 8A and 24A were produced according to the method of US Pat. No. 3,915,923. After the addition of the chain extenders, the mixture had to be stirred for 3 hours in order to obtain complete conversion or until the NCO content was constant. After the solvent had been distilled off, the reaction mixtures were nevertheless still highly viscous and not solid at room temperature. The reaction times, compared with the reaction times of the process according to the invention (maximum 3 minutes), were very long. Due to the very low solution viscosities, which correspond to a low molecular weight, and the plasticity at room temperature, both products could not be processed thermoplastically in an injection molding machine for further mechanical measurements. The processes with the addition of solvents cannot be used economically in TPU production because the solvent would have to be completely removed after the reaction, which is extremely expensive.

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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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un nouveau procédé de production de polyuréthanes pouvant être traités thermoplastiquement, des polyuréthanes pouvant être traités thermoplastiquement pouvant être obtenus par le procédé, des compositions, des articles et des utilisations desdits polyuréthanes.
EP20751142.9A 2019-08-07 2020-08-04 Procédé de production de polymères de polyuréthane pouvant être traités thermoplastiquement Pending EP4010390A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19190579.3A EP3772519A1 (fr) 2019-08-07 2019-08-07 Procédé de production de polymères de polyuréthane thermoplastiquement façonnables
PCT/EP2020/071929 WO2021023750A1 (fr) 2019-08-07 2020-08-04 Procédé de production de polymères de polyuréthane pouvant être traités thermoplastiquement

Publications (1)

Publication Number Publication Date
EP4010390A1 true EP4010390A1 (fr) 2022-06-15

Family

ID=67587410

Family Applications (2)

Application Number Title Priority Date Filing Date
EP19190579.3A Withdrawn EP3772519A1 (fr) 2019-08-07 2019-08-07 Procédé de production de polymères de polyuréthane thermoplastiquement façonnables
EP20751142.9A Pending EP4010390A1 (fr) 2019-08-07 2020-08-04 Procédé de production de polymères de polyuréthane pouvant être traités thermoplastiquement

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP19190579.3A Withdrawn EP3772519A1 (fr) 2019-08-07 2019-08-07 Procédé de production de polymères de polyuréthane thermoplastiquement façonnables

Country Status (6)

Country Link
US (1) US12240937B2 (fr)
EP (2) EP3772519A1 (fr)
JP (1) JP2022543416A (fr)
KR (1) KR20220045957A (fr)
CN (1) CN114174369B (fr)
WO (1) WO2021023750A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP3812407A1 (fr) * 2019-10-23 2021-04-28 Covestro Deutschland AG Polymère de polyuréthane présentant une dureté de <= 60 shore a
EP4342924A1 (fr) * 2022-09-26 2024-03-27 Covestro Deutschland AG Procédé de préparation de polyuréthanes thermoplastiques contenant du polyéther

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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
EP3812407A1 (fr) * 2019-10-23 2021-04-28 Covestro Deutschland AG Polymère de polyuréthane présentant une dureté de <= 60 shore a

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Publication number Priority date Publication date Assignee Title
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
EP3812407A1 (fr) * 2019-10-23 2021-04-28 Covestro Deutschland AG Polymère de polyuréthane présentant une dureté de <= 60 shore a

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US12240937B2 (en) 2025-03-04
US20220282022A1 (en) 2022-09-08
CN114174369A (zh) 2022-03-11
CN114174369B (zh) 2024-10-18
KR20220045957A (ko) 2022-04-13
WO2021023750A1 (fr) 2021-02-11
JP2022543416A (ja) 2022-10-12
EP3772519A1 (fr) 2021-02-10

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