EP4017901A1 - Procédé de préparation d'alcools de polyéthercarbonate - Google Patents

Procédé de préparation d'alcools de polyéthercarbonate

Info

Publication number
EP4017901A1
EP4017901A1 EP20751584.2A EP20751584A EP4017901A1 EP 4017901 A1 EP4017901 A1 EP 4017901A1 EP 20751584 A EP20751584 A EP 20751584A EP 4017901 A1 EP4017901 A1 EP 4017901A1
Authority
EP
European Patent Office
Prior art keywords
carbonate
catalyst
functional starter
starter substance
polyether
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
EP20751584.2A
Other languages
German (de)
English (en)
Inventor
Aurel Wolf
Mike SCHÜTZE
Stefan WESTHUES
Christoph Gürtler
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
Covestro Intellectual Property GmbH and Co KG
Original Assignee
Covestro Deutschland AG
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
Priority claimed from EP19192409.1A external-priority patent/EP3783046A1/fr
Application filed by Covestro Deutschland AG, Covestro Intellectual Property GmbH and Co KG filed Critical Covestro Deutschland AG
Publication of EP4017901A1 publication Critical patent/EP4017901A1/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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/30—General preparatory processes using carbonates
    • C08G64/305—General preparatory processes using carbonates and alcohols
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated

Definitions

  • the present invention relates to a process for the production of polyether carbonate alcohols, preferably polyether carbonate polyols, by the catalytic addition of cyclic ethylene carbonate to an H-functional starter substance.
  • cyclic carbonates such as cyclic propylene carbonate can be used as monomers in the manufacture of polycarbonate polyols.
  • This reaction is based on a transesterification and is carried out in the presence of catalysts such as titanium compounds such as titanium dioxide or titanium tetrabutoxide (EP 0 343 572), tin compounds such as tin dioxide or dibutyltin oxide (DE 2 523 352), or alkali metal carbonates or acetates ( DE 1 495 299 A1).
  • catalysts such as titanium compounds such as titanium dioxide or titanium tetrabutoxide (EP 0 343 572), tin compounds such as tin dioxide or dibutyltin oxide (DE 2 523 352), or alkali metal carbonates or acetates ( DE 1 495 299 A1).
  • the carbonates and alcohols used are incorporated alternately and thus alternating polycarbonate polyols are obtained.
  • These alternating polycarbonate polyols do not contain any ether groups
  • the object on which the present invention is based was to provide a process for the preparation of polyether carbonate alcohols with an increased proportion of incorporated CCh groups.
  • an H-functional starter substance and cyclic ethylene carbonate can first be placed in the reactor. It is also possible to initially charge only a portion of the H-functional starter substance and / or a portion of cyclic ethylene carbonate in the reactor. The amount of catalyst required for the ring-opening polymerization is then optionally added to the reactor. The order in which they are added is not critical.
  • the reactor can also be filled first with the catalyst and then an H-functional starter substance and cyclic ethylene carbonate. Alternatively, the catalyst can first be suspended in a functional starter substance and then the suspension can be filled into the reactor.
  • the molar ratio of H-functional starter substance to cyclic ethylene carbonate is in the range from more than 1: 1 to 1:20, particularly preferably 1: 2 to 1:15, particularly preferably 1: 5 to 1:10.
  • the catalyst is preferably used in an amount such that the content of catalyst in the resulting reaction product is 10 to 50,000 ppm, particularly preferably 20 to 30,000 ppm and most preferably 50 to 20,000 ppm.
  • the catalyst content is preferably determined by elemental analysis with optical emission spectrometry by means of inductively coupled plasmas (ICP-OES).
  • the resulting mixture of (a) a portion of H-functional starter substance, (b) catalyst and (c) cyclic ethylene carbonate is added at a temperature from 20 ° C to 120 ° C, particularly preferably from 40 ° C to 100 ° C inert gas (for example argon or nitrogen) introduced.
  • inert gas for example argon or nitrogen
  • an inert gas for example argon or nitrogen
  • the catalyst can be added in solid form or as a suspension in the cyclic ethylene carbonate, in an H-functional starter substance or in a mixture of the above.
  • a portion of the H-functional starter substances and cyclic ethylene carbonate is initially introduced in a first step and, in a subsequent second step, the temperature of the portion of H-functional starter substance and the cyclic ethylene carbonate is 40 ° C to 120 ° C, preferably 40 ° C to 100 ° C and / or the pressure in the reactor is reduced to less than 500 mbar, preferably 5 mbar to 100 mbar, where appropriate, a stream of inert gas (for example of argon or nitrogen) is applied and the catalyst to the partial amount of H- functional starter substance in the first step or immediately is then added in the second step.
  • inert gas for example of argon or nitrogen
  • the resulting reaction mixture is then heated at a temperature of 130 ° C to 230 ° C, preferably 140 ° C to 200 ° C, particularly preferably 160 ° C to 190 ° C, with an inert gas stream (for example of argon or nitrogen) if necessary can be passed through the reactor.
  • the reaction is continued until no more gas evolution is observed at the set temperature.
  • the reaction can also be carried out under pressure, preferably at a pressure of 50 mbar to 100 bar (absolute), particularly preferably 200 mbar to 50 bar (absolute), particularly preferably 500 mbar to 30 bar (absolute).
  • the remaining amount of bi-functional starter substance and / or cyclic ethylene carbonate is metered into the reactor continuously. It is possible to meter in the cyclic ethylene carbonate at a constant metering rate or to increase or decrease the metering rate gradually or stepwise or to add the cyclic ethylene carbonate in portions.
  • the cyclic ethylene carbonate is preferably added to the reaction mixture at a constant metering rate.
  • the cyclic ethylene carbonate or the bi-functional starter substances can be metered in simultaneously or sequentially via separate meterings (additions) in each case or via one or more meterings, the H-functional starter substances being metered in individually or as a mixture.
  • further cyclic carbonate in addition to the cyclic ethylene carbonate, further cyclic carbonate can optionally be used in a proportion of at most 20% by weight, preferably at most 10% by weight, particularly preferably at most 5% by weight, based in each case on the sum of the total weight of cyclic carbonate.
  • Propylene carbonate is preferably used as a further cyclic carbonate. However, it is very particularly preferred that only cyclic ethylene carbonate is used.
  • the polyether carbonate alcohols can be produced in a batch, semi-batch or continuous process.
  • the polyether carbonate alcohols are preferably produced in a continuous process which comprises both continuous copolymerization and continuous addition of the H-functional starter substance.
  • the invention therefore also relates to a process in which H-functional starter substance, cyclic ethylene carbonate and catalyst are continuously metered into the reactor and the resulting reaction mixture (containing the reaction product) is continuously removed from the reactor.
  • the catalyst is preferably added continuously suspended in H-functional starter substance.
  • the term "continuously" as used herein can be used as a mode of adding a relevant Catalyst or reactants are defined so that a substantially continuous effective concentration of the catalyst or reactants is maintained.
  • the supply of the catalyst and the reactants can be carried out really continuously or in relatively closely spaced increments.
  • a continuous addition of starter can be genuinely continuous or take place in increments. It would not deviate from the present method to add a catalyst or reactants incrementally in such a way that the concentration of the added materials falls essentially to zero for some time before the next incremental addition.
  • the catalyst concentration be maintained at substantially the same concentration during the main part of the course of the continuous reaction and that initiator substance be present during the main part of the polymerization process.
  • Suitable H-functional starter substances which can be used are compounds with H atoms active for the alkoxylation, which have a number average molecular weight according to DIN55672-1 up to 10,000 g / mol, preferably up to 5000 g / mol and particularly preferably up to 2500 g / mol.
  • Groups with active H atoms which are active for the alkoxylation are, for example, -OH, -NH2 (primary amines), -NH- (secondary amines), -SH and -CO2H, preferred are -OH, -NH2 and -CO2H, particularly preferred -OH.
  • one or more compounds are selected from the group consisting of monohydric or polyhydric alcohols, polyhydric amines, polyhydric thiols, amino alcohols, thioalcohols, hydroxyesters, polyether polyols, polyester polyols, polyester ether polyols, polyether carbonate polyols, polycarbonate polyols, polycarbonates, polyethylene imines, polyetheramines, polytetrahydrofurans (z. B.
  • PolyTHF ® of BASF Polytetrahydrofuranamine, Polyetherthiole, polyacrylate polyols, castor oil, the mono- or di-glyceride of ricinoleic acid, monoglycerides of Fehklaren, chemically modified mono-, di- and / or triglycerides of Fehklaren, and C1 -C24 alkyl malic acid esters that contain at least 2 OH groups per molecule in the Mihel and water.
  • the C1-C24 alkyl malic acid esters which contain at least 2 OH groups per molecule in the Mihel, are commercial products such as Fupranol Balance ® (BASF AG), Merginol ® types (Hobum Oleochemicals GmbH), Sovermol ® types (from Cognis GmbH & Co. KG) and Soyol ® TM types (from USSC Co.).
  • Fupranol Balance ® BASF AG
  • Merginol ® types Hobum Oleochemicals GmbH
  • Sovermol ® types from Cognis Deutschland GmbH & Co. KG
  • Soyol ® TM types from USSC Co.
  • Alcohols, amines, thiols and carboxylic acids can be used as monofunctional starter substances become.
  • the following can be used as monofunctional alcohols: methanol, ethanol, 1-propanol,
  • Possible monofunctional amines are: butylamine, tert-butylamine, pentylamine, hexylamine, aniline, aziridine, pyrrolidine, piperidine, morpholine.
  • the following monofunctional thiols can be used: ethanethiol, 1-propanethiol, 2-propanethiol, 1-butanethiol, 3-methyl-1-butanethiol, 2-butene-1-thiol, thiophenol.
  • carboxylic acids formic acid, acetic acid, propionic acid, butyric acid, acrylic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, aromatic carboxylic acids such as benzoic acid, terephthalic acid, tetrahydrophthalic acid, phthalic acid or isophthalic acid, such as palmitic acid, fatty acids Linolenic acid.
  • Polyhydric alcohols suitable as H-functional starter substance are, for example, dihydric alcohols (such as, for example, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-propanediol, 1,4-butanediol, 1,4-butenediol, 1,4-butynediol, neopentyl glycol, 1 , 5-pentanediol, methylpentanediols (such as 3-methyl-1,5-pentanediol), 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, bis (hydroxymethyl) - cyclohexanes (such as 1,4-bis (hydroxymethyl) cyclohexane, triethylene glycol, tetraethylene glycol, polyethylene glycols, dipropylene glycol
  • the H-functional starter substance can also be selected from the substance class of polyether polyols which have a molecular weight M n according to DIN55672-1 in the range from 18 to 8000 g / mol and a functionality of 2 to 3. Preference is given to polyether polyols which are built up from repeating ethylene oxide and propylene oxide units, preferably with a proportion of 35 to 100% propylene oxide units, particularly preferably with a proportion of 50 to 100% propylene oxide units. These can be random copolymers, gradient copolymers, alternating or block copolymers of ethylene oxide and propylene oxide.
  • the H-functional starter substance can also be selected from the substance class of polyester polyols. At least difunctional polyesters are used as polyester polyols. Polyester polyols preferably consist of alternating acid and alcohol units.
  • acid components for example Succinic acid, maleic acid, maleic anhydride, adipic acid, phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride or mixtures of the acids and / or anhydrides mentioned are used.
  • acid components for example Succinic acid, maleic acid, maleic anhydride, adipic acid, phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride or mixtures of the acids and / or anhydrides mentioned are
  • ethanediol 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,4-bis (hydroxymethyl) cyclohexane, diethylene glycol, Dipropylene glycol, trimethylolpropane, glycerol, pentaerythritol or mixtures of the alcohols mentioned are used. If dihydric or polyhydric polyether polyols are used as the alcohol component, polyester ether polyols are obtained which can also serve as starter substances for the preparation of the polyether carbonate alcohols.
  • polycarbonate diols can be used as H-functional starter substance, which are produced, for example, by reacting phosgene, dimethyl carbonate, diethyl carbonate or diphenyl carbonate and difunctional alcohols or polyester polyols or polyether polyols.
  • polycarbonates can be found e.g. B. in EP-A 1359177.
  • polyether carbonate polyols can be used as H-functional starter substance.
  • polyether carbonate polyols obtainable by the process according to the invention described here are used. These polyether carbonate polyols used as H-functional starter substances are prepared beforehand in a separate reaction step for this purpose.
  • the H-functional starter substance generally has a functionality (i.e. number of H atoms active for the polymerization per molecule) of 1 to 8, preferably 1 to 3.
  • the H-functional starter substance is used either individually or as a mixture of at least two H-functional starter substances.
  • the H-functional starter substance is particularly preferably at least one compound selected from the group consisting of water, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol , 2-methylpropane-l, 3-diol, neopentyl glycol, 1,6-hexanediol, 1,8-octanediol, diethylene glycol, dipropylene glycol, glycerol, trimethylolpropane, pentaerythritol, sorbitol, polyether carbonate polyols with a molecular weight M n according to DIN55672-1 in the range of 150 to 8000 g / mol with a functionality of 2 to 3 and polyether polyols with a molecular weight M n according to DIN55672-1 in the range from 150 to 8000 g / mol and
  • the H-functional starter substance is preferably chosen such that a polyether carbonate polyol, i.e. a polyether carbonate alcohol with a functionality of 2 or more, is obtained as the polyether carbonate alcohol.
  • the catalyst used is at least one compound according to one of the formulas X [V0 3 ] (1)
  • An alkali metal is used as the cation X, preferably potassium or cesium, particularly preferably potassium.
  • the cation Y used in formula (2) and (3) is potassium or cesium, preferably potassium.
  • a compound of the formula (1) or (3), particularly preferably of the formula (1), is preferably used as the catalyst.
  • At least one compound selected from the group consisting of KV0 3 , CsV0 3 , K 3 V0 4 , Cs 3 V0 4 , K 2 W0 4 and CsW0 4 is used as the catalyst.
  • polyether carbonate alcohols obtained by the process according to the invention can be processed further to form polyurethanes, for example by reaction with di- and / or polyisocyanates.
  • detergent formulations such as for textile or surface cleaning, drilling fluids, fuel additives, ionic and non-ionic surfactants, dispersants, lubricants, process chemicals for paper or textile production, cosmetic formulations, such as in skin or sun protection cream or hair care products.
  • GPC measurements were made at 40 ° C. in tetrahydrofuran (THF, flow rate: 1.0 mF / min) according to DIN 55672-1.
  • the column set consisted of the following five columns: PSS, 5 pF, 8x50 mF guard column, 2 PSS SVD, 5 pF, 100 ⁇ , 8x300mm, 2 PSS SVD, 5 pF, 1000 ⁇ , 8x300mm)).
  • Samples (concentration 2-3 g Fl, injection volume 100 pF) were injected with an Agilent technologies 1100.
  • An Agilent 1200 series RID detector was used to detect the concentration of substances at the end of the columns.
  • the raw files were processed with a PSS WinGPC Unity software package.
  • Polystyrene of known molecular weight was used to calibrate the GPC and to reference the molecular weight distribution (PSS ReadyCal Kit ranging from 266 Da to 66,000 Da was used).
  • the number average molecular weight was determined by GPC and is reported as M n in the examples.
  • the proportion of incorporated CO2 in the resulting polyether carbonate alcohol (CCF content) was determined by means of 'H-NMR spectroscopy (Bruker Company, AV III HD 600, 600 MHz; pulse program zg30, waiting time dl: 10s, 64 scans). Each sample was dissolved in deuterated chloroform.
  • F (4.37-4.21) area of resonance at 4.37-4.21 ppm for polyether carbonate alcohol.
  • F (4, 19-4.07) area of resonance at 4.19-4.07 ppm for polyether carbonate alcohol (The sum of F (4.37-4.21) and F (4, 19-4.07) corresponds to 4 protons)
  • N [(4, 37-4, 21) + F (4, 19-4, 07)] x 88 + F (3, 8 - 3, 55) x 44 (P)
  • the factor 88 results from the sum of the molar masses of CO2 (molar mass 44 g / mol) and that of ethylene oxide (molar mass 44 g / mol), the factor 44 results from the molar mass of ethylene oxide.
  • the weight fraction (in% by weight) of CO2 in the polyether carbonate alcohol was calculated according to formula (III):
  • the non-polymer components of the reaction mixture i.e. unreacted cyclic ethylene carbonate
  • the specification of the CCF content in the polyether carbonate alcohol ("built-in CO2"; see the following examples) is standardized to the polyether carbonate alcohol molecule that was created during the ring-opening polymerization.
  • Example 1 Preparation of polyether carbonate alcohols by ring-opening polymerization of cyclic ethylene carbonate in the presence of 1,6-hexanediol as starter and NasVCü as catalyst
  • a 500 mL four-necked glass flask was equipped with a reflux condenser, KPG stirrer, thermal sensor, nitrogen inlet and gas outlet / gas outlet with pressure relief valve. Then 200 g of cyclic ethylene carbonate, 37.9 g of 1,6-hexanediol and 2.1 g of NaWCE were weighed out. 10 L / h of nitrogen was passed in for 30 minutes, the suspension being stirred at 300 rpm has been. The suspension was then gradually heated to 180 ° C. The resulting gas stream was drained through a bubble counter after the reflux condenser.
  • the reaction mixture was kept at the set temperature until the evolution of gas came to a standstill.
  • the CCh fraction built into the polyether carbonate alcohol was determined using the methods described above by means of 'H-NMR spectroscopy.
  • the molecular weight was determined by means of gel permeation chromatography.
  • Example 2 Preparation of polyether carbonate alcohols by ring-opening polymerization of cyclic ethylene carbonate in the presence of 1,6-hexanediol as starter and K3VO4 as catalyst
  • Example 3 Preparation of polyether carbonate alcohols by ring-opening polymerization of cyclic ethylene carbonate in the presence of 1,6-hexanediol as starter and CS3VO4 as catalyst
  • Example 4 Preparation of polyether carbonate alcohols by ring-opening polymerization of cyclic ethylene carbonate in the presence of 1,6-hexanediol as starter and KVO3 as catalyst
  • Example 5 Preparation of polyether carbonate alcohols by ring-opening polymerization of cyclic ethylene carbonate in the presence of 1,6-hexanediol as starter and CsVCb as catalyst
  • the catalysts used in Examples 1 to 5 lead to the addition of cyclic ethylene carbonate onto an H-functional starter substance.
  • the catalysts according to the invention lead to an increased incorporation of CCE groups into the polyether carbonate alcohols of Examples 2 to 5 in contrast to Example 1.
  • a catalyst of the formula (1) is used.
  • the catalysts of the invention additionally have an increased catalytic activity, which leads to an increase in the molecular weight of the polyether carbonate alcohols obtained in Examples 4 and 5 compared to Examples 2 and 3.

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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)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne un procédé de préparation d'alcools de polyéthercarbonate par fixation de carbonate d'éthylène cyclique à une substance de départ à fonction H en présence d'un catalyseur, caractérisé en ce qu'au moins un composé selon les formules X[VO3] (1), Y2[WO4] (2), ouY3[VO4] (3), dans laquelle X = un métal alcalin, de préférence, du potassium ou du césium, et Y = du potassium ou du césium, est utilisé.
EP20751584.2A 2019-08-19 2020-08-12 Procédé de préparation d'alcools de polyéthercarbonate Pending EP4017901A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP19192409.1A EP3783046A1 (fr) 2019-08-19 2019-08-19 Procédé de fabrication de polyols de poly(éther-carbonate)
EP20158918 2020-02-24
PCT/EP2020/072585 WO2021032555A1 (fr) 2019-08-19 2020-08-12 Procédé de préparation d'alcools de polyéthercarbonate

Publications (1)

Publication Number Publication Date
EP4017901A1 true EP4017901A1 (fr) 2022-06-29

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Application Number Title Priority Date Filing Date
EP20751584.2A Pending EP4017901A1 (fr) 2019-08-19 2020-08-12 Procédé de préparation d'alcools de polyéthercarbonate

Country Status (4)

Country Link
US (1) US20220267504A1 (fr)
EP (1) EP4017901A1 (fr)
CN (1) CN114206983A (fr)
WO (1) WO2021032555A1 (fr)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1495299A1 (de) 1963-05-09 1969-01-02 Huels Chemische Werke Ag Verfahren zur Herstellung linearer Polycarbonate
DE2523352A1 (de) 1975-05-27 1976-12-09 Bayer Ag Verfahren zur herstellung aliphatischer polycarbonate
EP0343572B1 (fr) 1988-05-26 1996-10-02 Daicel Chemical Industries, Ltd. Composition de diol de polycarbonate et résine de polyuréthane
DE10219028A1 (de) 2002-04-29 2003-11-06 Bayer Ag Herstellung und Verwendung von hochmolekularen aliphatischen Polycarbonaten
EP2115032B2 (fr) * 2007-01-30 2014-10-22 Basf Se Procédé de production de polyéthercarbonate polyols
KR101867384B1 (ko) * 2012-09-12 2018-07-23 에스케이이노베이션 주식회사 폴리카보네이트의 제조방법 및 이에 따라 제조된 폴리카보네이트
EP2837648A1 (fr) * 2013-08-12 2015-02-18 Repsol, S.A. Procédé pour la préparation d'un polycarbonate polyol
EP3164442B1 (fr) * 2014-07-03 2018-08-29 Covestro Deutschland AG Procédé destiné à la fabrication de polyéthercarbonatpolyoles
EP3219741A1 (fr) * 2016-03-18 2017-09-20 Covestro Deutschland AG Procede de production de polyethercarbonatpolyoles

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US20220267504A1 (en) 2022-08-25
CN114206983A (zh) 2022-03-18
WO2021032555A1 (fr) 2021-02-25

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