WO2008104541A1 - Procédé de production d'alcools de polyester - Google Patents

Procédé de production d'alcools de polyester Download PDF

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Publication number
WO2008104541A1
WO2008104541A1 PCT/EP2008/052316 EP2008052316W WO2008104541A1 WO 2008104541 A1 WO2008104541 A1 WO 2008104541A1 EP 2008052316 W EP2008052316 W EP 2008052316W WO 2008104541 A1 WO2008104541 A1 WO 2008104541A1
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WO
WIPO (PCT)
Prior art keywords
alcohols
carboxylic acid
acid
functional
succinic acid
Prior art date
Application number
PCT/EP2008/052316
Other languages
German (de)
English (en)
Inventor
Lionel Gehringer
Mirko Kreitschmann
Edzard Scholten
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of WO2008104541A1 publication Critical patent/WO2008104541A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof

Definitions

  • the invention relates to a process for the preparation of polyester alcohols, the polyester alcohols prepared by this process and their use for the preparation of polyurethanes.
  • polyester alcohols by polycondensation reactions of polybasic carboxylic acids with polyhydric alcohols or polyols has been described many times.
  • polyester alcohols are preferably carried out for the production of polyurethanes, hereinafter also referred to as PUR, in particular of flexible polyurethane foam, rigid polyurethane foam or non-cellular PUR materials.
  • PUR polyurethanes
  • the different fields of application require a concrete selection of the input products and the polycondensation technology to be carried out.
  • polyfunctional aromatic and / or aliphatic carboxylic acids or their anhydrides and di-, tri- and / or higher-functional alcohols, in particular glycols for the preparation of the polyester alcohols.
  • the starting materials are usually reacted at temperatures of 150-280 0 C under atmospheric pressure and or a slight vacuum in the presence of catalysts with removal of the water of reaction with each other to implement.
  • the usual technology is z.
  • polybasic carboxylic acids it is possible to use both aromatic carboxylic acids, in particular phthalic acid, isophthalic acid or terephthalic acid, or aliphatic carboxylic acids.
  • adipic acid has the greatest technical importance.
  • succinic acid optionally in admixture with other carboxylic acids, is used.
  • Succinic acid is used, for example, for the production of biodegradable products.
  • Succinic acid can be produced by petrochemical or microbial fermentation of carbohydrates. It is generally desirable to increase the share of products based on renewable raw materials.
  • a microbacterial synthesis for the production of succinic acid is described for example in US 5,869,301.
  • the organically produced succinic acid usually has an increased content of compounds containing nitrogen atoms. These compounds can have a very disadvantageous effect especially in the further processing of succinic acid to polyester alcohols and their conversion to polyurethanes.
  • JP 2005-139287 describes a process for the preparation of polyesters prepared using biologically produced succinic acid.
  • the succinic acid was purified after separation from the fermentation by repeated recrystallization.
  • the polyesters produced using succinic acid have a nitrogen compound content of less than 1000 ppm.
  • the polyesters are not polyester alcohols, ie intermediates for further processing, but finished products.
  • polyester alcohols which are produced on the basis of renewable raw materials. They should be manufacturable without problems and can be processed into polyurethanes with good performance properties.
  • the object could be achieved by using succinic acid, which was produced biologically by fermentation of carbohydrates, for the production of the polyester alcohols.
  • the invention accordingly provides a process for the preparation of polyester alcohols by reacting
  • the invention furthermore relates to the polyester alcohols produced by the process according to the invention.
  • the invention further provides a process for the preparation of polyurethanes by reacting A) polyisocyanates with B) compounds having at least two isocyanate-reactive hydrogen atoms, characterized in that as compounds at least two isocyanate-reactive hydrogen atoms B) the polyester alcohols according to the invention are used.
  • the preparation of the polyester alcohols by the process according to the invention is carried out as described by reacting succinic acid, which has been produced biologically by fermentation of carbohydrates, with at least difunctional alcohols.
  • succinic acid can be formed by anaerobic microorganisms as a fermentation product of sugars and cellulose.
  • the separation of the succinic acid can take place in the form of their salts and esters by means of electrodialysis.
  • succinic acid ai produced by biological processes has a content of nitrogen. This results mostly from degradation products in the biological production of succinic acid by means of bacteria.
  • the content of nitrogen expressed as elemental nitrogen, depending on the production and the purification of the succinic acid, usually in the range between greater than 0 and 500 ppm.
  • the biologically produced succinic acid ai) can surprisingly be used without any problems for the preparation of polyester alcohols.
  • the nitrogen atom-containing compounds have no negative effect on the reaction of succinic acid with the alcohols and on the processing properties of the resulting polyester alcohols. This was due to the catalytic effect of such compounds, especially in the production of polyurethanes, not expected for the skilled person.
  • the biologically-derived succinic acid ai) may be used alone or in combination with other at least difunctional carboxylic acids aii).
  • the succinic acid is used in admixture with other at least difunctional carboxylic acids, since polyester alcohols, in the production of which only succinic acid was used, often have insufficient hydrolytic stability, an increased viscosity and an undesirable crystallization tendency.
  • the biologically produced succinic acid ai) is preferably used in a mixture with other at least difunctional carboxylic acids aii). In principle, all known at least difunctional carboxylic acids can be used for this purpose. These can be used as acid and / or in the form of the anhydrides.
  • At least difunctional aromatic carboxylic acids such as phthalic acid, phthalic anhydride, isophthalic acid or terephthalic acid.
  • the biologically prepared succinic acid ai) is preferably used in admixture with aliphatic at least difunctional carboxylic acids aii). In the simplest case, this may be succinic acid prepared by another process. An aliphatic at least difunctional carboxylic acid other than succinic acid is preferably used.
  • the aliphatic at least difunctional carboxylic acids are preferably selected from the group comprising oxalic acid, malonic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and adipic acid.
  • the at least two-functional aliphatic carboxylic acid aii) is adipic acid.
  • the weight ratio of the carboxylic acid ai) to the carboxylic acid aii) is in the range from 10:90 to 90:10, particularly preferably in the range from 70:30 to 30:70.
  • the polyhydroxy compound are all at least dihydric alcohols, preferably di- to six-functional compounds such as monoethylene glycol, diethylene glycol, monopropylene glycol, dipropylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 2-methyl-1, 3rd propanediol, 3-methyl-1, 5-pentanediol, neopentyl glycol, glycerin, trimethylopropane, pentaerythritol and sorbitol.
  • the trihydric or higher functional alcohols serve to increase the functionality of the polyester alcohols.
  • alcohols bi) are glycerol, trimethylolpropane, pentaerythritol and sorbitol.
  • the higher-functional compounds are used in particular for the production of polyether alcohols for hard foam applications. It is also possible to use oligomeric or polymeric products having at least two hydroxyl groups. Examples of these are polytetrahydrofuran, polylactones, polyglycerol, polyether alcohols, polyester alcohols or ⁇ , ⁇ -dihydroxypolybutadiene.
  • difunctional alcohols in particular monoethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol or mixtures of at least two of the diols mentioned.
  • the at least difunctional alcohol is particularly preferably monoethylene glycol or mixtures of monoethylene glycol with at least one further alcohol.
  • the preparation of the polyester alcohols is, as described, carried out by reacting the polyfunctional carboxylic acids with the polyfunctional alcohols with removal of the water.
  • a stirred tank reactor with stirrer and distillation column is used to carry out the process.
  • This apparatus is usually a closed system and can generally be evacuated by means of a vacuum pump.
  • the educts are heated with stirring and preferably with exclusion of air (for example in a nitrogen atmosphere or under reduced pressure).
  • the water formed in the polycondensation is preferably distilled off at low pressure or a continuously decreasing pressure (see Batchwise Vacuum-Melt method, Houben-Weyl 14/2, 2).
  • the reaction temperature is preferably between 150 and 280 0 C.
  • the pressure is gradually reduced in the course of the reaction, the final pressure is preferably below 200 mbar. At this pressure, the reaction is continued until the desired degree of conversion.
  • the reaction may be catalyst-free or, preferably, in the presence of esterification catalysts, conveniently in an atmosphere of inert gases, e.g. Nitrogen, helium, or argon take place.
  • inert gases e.g. Nitrogen, helium, or argon take place.
  • acidic catalysts such as toluenesulfonic acids, but preferably organometallic compounds, in particular those based on titanium or tin, such as titanium tetrabutoxide or tin (II) octoate, dibutyltin dilaurate, tin chloride.
  • the organic carboxylic acids and polyhydric alcohols are preferably polycondensed in a molar ratio of 1: 1, 01 to 1, 8, preferably 1: 1, 05 to 1, 2.
  • the polyester alcohols according to the invention preferably have a hydroxyl number in the range between 30 and 600 mg KOH / g and an acid number of not more than 2 mg KOH / g.
  • novel compounds can preferably be used for the preparation of polyurethanes. For this you are reacted with at least two-functional isocyanates.
  • the polyurethanes may be the usual and known compounds, for example compact polyurethanes, such as cast elastomers or thermoplastic elastomers. If blowing agents are present during the reaction, polyurethane foams are formed. Depending on the formulation, these may be rigid foams, flexible foams or microcellular elastomers.
  • thermoplastic elastomers TPU
  • TPU thermoplastic elastomers
  • thermoplastic elastomers The preparation of the thermoplastic elastomers is carried out by reacting diisocyanates with compounds having at least two isocyanate-reactive hydrogen atoms, preferably difunctional alcohols.
  • Suitable diisocyanates are customary aromatic, aliphatic and / or cycloaliphatic diisocyanates, for example diphenylmethane diisocyanate (MDI), tolylene diisocyanate (TDI), tri-, tetra-, penta-, hexa-, hepta- and / or octamethylene diisocyanate, 2-methyl pentamethylene diisocyanate 1, 5, 2-ethyl butylene diisocyanate 1, 4, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl cyclohexane (isophorone diisocyanate, IPDI), 1, 4 and / or 1, 3-bis (isocyanatomethyl) cyclohexane (HXDI), 1,4-cyclohexane diisocyanate, 1-methyl-2,4- and / or -2,6-cyclohexane diisocyanate, 4,4'-, 2,4'
  • polyester alcohols according to the invention are used.
  • generally known polyhydroxyl compounds having molecular weights of 500 to 8,000, preferably 600 to 6,000, especially 800 to 4,000, and preferably an average functionality of 1, 8 to 2.6, preferably 1, 9 to 2.2, in particular 2 be used, for example, polyester alcohols, polyether alcohols and / or polycarbonate diols.
  • Isocyanate-reactive compounds also include chain extenders.
  • chain extenders it is possible to use generally known, especially difunctional compounds, for example diamines and / or alkanediols having 2 to 10 C atoms in the alkylene radical, in particular ethylene glycol and / or butanediol-1, 4, and / or hexanediol and / or di- and / or Tri-oxyalkylen- glycols having 3 to 8 carbon atoms in the oxyalkylene, preferably corresponding oligo-polyoxypropylene glycols, mixtures of the chain extenders can be used.
  • difunctional compounds for example diamines and / or alkanediols having 2 to 10 C atoms in the alkylene radical, in particular ethylene glycol and / or butanediol-1, 4, and / or hexanediol and / or di- and / or Tri-oxyalkylen- glycol
  • chain extender 1,4-bis- (hydroxymethyl) - benzene (1,4-BHMB), 1,4-bis (hydroxyethyl) benzene (1,4-BHEB) or 1,4-bis (2-hydroxyethoxy) benzene (1,4-HQEE) come.
  • Preferred chain extenders are ethylene glycol and hexanediol, particularly preferably ethylene glycol.
  • catalysts which accelerate the reaction between the NCO groups of the diisocyanates and the hydroxyl groups of the synthesis components, for example tertiary amines, such as triethylamine, dimethylcyclohexylamine, N-methylmorpholine, N, N'-dimethylpiperazine, 2- (dimethylaminoethoxy) - ethanol, diazabicyclo- (2,2,2) octane and the like, and in particular organic metal compounds such as titanic acid esters, iron compounds such as Iron (I M) acetylacetonate, tin compounds such as tin diacetate, tin dilaurate or the tin dialkyl salts of aliphatic carboxylic acids such as dibutyltin diacetate, dibutyltin dilaurate or the like.
  • the catalysts are usually used in amounts of 0.0001 to 0.1 parts by weight per 100 parts by weight of polyhydroxyl compound.
  • catalysts can be added to the structural components to also conventional auxiliaries. Mention may be made, for example, of surface-active substances, flame retardants, nucleating agents, lubricants and mold release agents, dyes and pigments, inhibitors, stabilizers against hydrolysis, light, heat, oxidation or discoloration, protective agents against microbial degradation, inorganic and / or organic fillers, reinforcing agents and plasticizers.
  • the preparation of the TPU is usually carried out by conventional methods, such as by belt systems or by means of reaction extruders.
  • polyurethanes produced according to the invention have comparable properties to those based on petrochemically produced succinic acid. Also in the production of polyurethanes there are no differences to other products.
  • the resulting brown, liquid polyester alcohol had the following characteristics:
  • Viscosity 700 mPa s at 75 0 C.
  • the resulting brown, liquid polyester alcohol had the following characteristics:
  • thermoplastic polyurethanes As can be seen, there are no differences in the properties of the thermoplastic polyurethanes.

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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 procédé de production d'alcools de polyester par réaction a) d'au moins un acide carboxylique au moins bifonctionnel avec b) au moins un alcool au moins bifonctionnel. Selon l'invention, on utilise comme acide carboxylique bifonctionnel a) de l'acide succinique ai) qui a été produit biologiquement par fermentation d'hydrates de carbone.
PCT/EP2008/052316 2007-02-28 2008-02-26 Procédé de production d'alcools de polyester WO2008104541A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07103217.1 2007-02-28
EP07103217 2007-02-28

Publications (1)

Publication Number Publication Date
WO2008104541A1 true WO2008104541A1 (fr) 2008-09-04

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011125720A1 (fr) 2010-03-31 2011-10-13 三菱化学株式会社 Polyuréthane dérivé de ressources de biomasse, procédé pour produire celui-ci, et polyester-polyol dérivé de ressources de biomasse
EP2392602A2 (fr) 2010-06-02 2011-12-07 Bayer MaterialScience AG Polyuréthane pouvant être traité de manière thermoplastique à base d'acide de propionate succinité
US20120258269A1 (en) * 2009-12-16 2012-10-11 Basf Se Preparing polyester polyols
WO2013045546A1 (fr) 2011-09-30 2013-04-04 Bayer Intellectual Property Gmbh Articles homogènes extrudés à partir de polyuréthanes thermoplastiques à base de polyester diols de l'acide succinique et de 1,3-propanediol
WO2015000722A1 (fr) * 2013-07-02 2015-01-08 Basf Se Polyuréthane à base de matières premières renouvelables
EP2636694B1 (fr) 2012-03-09 2020-03-25 Oleon Nv Polyester polyéther polyol

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Publication number Priority date Publication date Assignee Title
EP0565235A2 (fr) * 1992-04-10 1993-10-13 Showa Highpolymer Co., Ltd. Polyester aliphatique contenant des liaisons uréthane
EP0569154A1 (fr) * 1992-05-08 1993-11-10 Showa Highpolymer Co., Ltd. Couche jetable biodégradable
JP2005139287A (ja) * 2003-11-06 2005-06-02 Mitsubishi Chemicals Corp ポリエステルの製造方法
JP2005163032A (ja) * 2003-11-13 2005-06-23 National Institute Of Advanced Industrial & Technology コハク酸アンモニウムを用いるポリエステルの製造方法
EP1882712A1 (fr) * 2005-04-22 2008-01-30 Mitsubishi Chemical Corporation Polyester derive de la biomasse et son procede de fabrication

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Publication number Priority date Publication date Assignee Title
EP0565235A2 (fr) * 1992-04-10 1993-10-13 Showa Highpolymer Co., Ltd. Polyester aliphatique contenant des liaisons uréthane
EP0569154A1 (fr) * 1992-05-08 1993-11-10 Showa Highpolymer Co., Ltd. Couche jetable biodégradable
JP2005139287A (ja) * 2003-11-06 2005-06-02 Mitsubishi Chemicals Corp ポリエステルの製造方法
JP2005163032A (ja) * 2003-11-13 2005-06-23 National Institute Of Advanced Industrial & Technology コハク酸アンモニウムを用いるポリエステルの製造方法
EP1882712A1 (fr) * 2005-04-22 2008-01-30 Mitsubishi Chemical Corporation Polyester derive de la biomasse et son procede de fabrication

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DATABASE WPI Week 200550, Derwent World Patents Index; AN 2005-490331, XP002475897 *

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120258269A1 (en) * 2009-12-16 2012-10-11 Basf Se Preparing polyester polyols
JP2013514406A (ja) * 2009-12-16 2013-04-25 ビーエーエスエフ ソシエタス・ヨーロピア ポリエステルポリオールの製造方法
US9963537B2 (en) 2010-03-31 2018-05-08 Mitsubishi Chemical Corporation Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol
WO2011125720A1 (fr) 2010-03-31 2011-10-13 三菱化学株式会社 Polyuréthane dérivé de ressources de biomasse, procédé pour produire celui-ci, et polyester-polyol dérivé de ressources de biomasse
US10619000B2 (en) 2010-03-31 2020-04-14 Mitsubishi Chemical Corporation Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol
US9394397B2 (en) 2010-03-31 2016-07-19 Mitsubishi Chemical Corporation Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol
US10351658B2 (en) 2010-03-31 2019-07-16 Mitsubishi Chemical Corporation Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol
EP3486267A1 (fr) 2010-03-31 2019-05-22 Mitsubishi Chemical Corporation Polyuréthane dérivé de ressources de biomasse, son procédé de production et polyester polyol dérivé de ressources de biomasse
KR101697889B1 (ko) 2010-03-31 2017-01-18 미쓰비시 가가꾸 가부시키가이샤 바이오매스 자원 유래 폴리우레탄 및 그 제조 방법 그리고 바이오매스 자원 유래 폴리에스테르폴리올
KR101640966B1 (ko) 2010-03-31 2016-07-21 미쓰비시 가가꾸 가부시키가이샤 바이오매스 자원 유래 폴리우레탄 및 그 제조 방법 그리고 바이오매스 자원 유래 폴리에스테르폴리올
KR20150088915A (ko) 2010-03-31 2015-08-03 미쓰비시 가가꾸 가부시키가이샤 바이오매스 자원 유래 폴리우레탄 및 그 제조 방법 그리고 바이오매스 자원 유래 폴리에스테르폴리올
CN105037683A (zh) * 2010-03-31 2015-11-11 三菱化学株式会社 来自生物质资源的聚氨酯、皮革和鞋底用聚氨酯
CN102822223B (zh) * 2010-03-31 2016-01-20 三菱化学株式会社 来自生物质资源的聚氨酯及其制造方法以及来自生物质资源的聚酯多元醇
US9290614B2 (en) 2010-03-31 2016-03-22 Mitsubishi Chemical Corporation Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol
KR20130009819A (ko) 2010-03-31 2013-01-23 미쓰비시 가가꾸 가부시키가이샤 바이오매스 자원 유래 폴리우레탄 및 그 제조 방법 그리고 바이오매스 자원 유래 폴리에스테르폴리올
CN102822223A (zh) * 2010-03-31 2012-12-12 三菱化学株式会社 来自生物质资源的聚氨酯及其制造方法以及来自生物质资源的聚酯多元醇
EP2392602A3 (fr) * 2010-06-02 2011-12-14 Bayer MaterialScience AG Polyuréthane pouvant être traité de manière thermoplastique à base d'acide de propionate succinité
EP2392602A2 (fr) 2010-06-02 2011-12-07 Bayer MaterialScience AG Polyuréthane pouvant être traité de manière thermoplastique à base d'acide de propionate succinité
US9458277B2 (en) 2011-09-30 2016-10-04 Covestro Deutschland Ag Homogeneous extruded articles made from thermoplastically processable polyurethanes based on polyester diols formed from succinic acid and 1,3-propanediol
CN104024297A (zh) * 2011-09-30 2014-09-03 拜耳知识产权有限责任公司 由基于由琥珀酸和1,3-丙二醇形成的聚酯二醇的可热塑性加工的聚氨酯制成的均匀挤出制品
RU2618219C2 (ru) * 2011-09-30 2017-05-03 Байер Интеллектуэль Проперти Гмбх Гомогенное экструдированное изделие из термопластично перерабатываемых полиуретанов на основе полиэфирдиолов из янтарной кислоты и 1,3-пропандиола
WO2013045546A1 (fr) 2011-09-30 2013-04-04 Bayer Intellectual Property Gmbh Articles homogènes extrudés à partir de polyuréthanes thermoplastiques à base de polyester diols de l'acide succinique et de 1,3-propanediol
CN104024297B (zh) * 2011-09-30 2016-05-18 拜耳知识产权有限责任公司 由基于由琥珀酸和1,3-丙二醇形成的聚酯二醇的可热塑性加工的聚氨酯制成的均匀挤出制品
EP2636694B2 (fr) † 2012-03-09 2023-03-01 Oleon Nv Polyester polyéther polyol
EP2636694B1 (fr) 2012-03-09 2020-03-25 Oleon Nv Polyester polyéther polyol
WO2015000722A1 (fr) * 2013-07-02 2015-01-08 Basf Se Polyuréthane à base de matières premières renouvelables
US20160152761A1 (en) * 2013-07-02 2016-06-02 Basf Se Polyurethane based on renewable raw materials
US11124594B2 (en) 2013-07-02 2021-09-21 Basf Se Polyurethane based on renewable raw materials

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