WO2011032914A1 - Polyéthers comportant des groupes silane - Google Patents

Polyéthers comportant des groupes silane Download PDF

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Publication number
WO2011032914A1
WO2011032914A1 PCT/EP2010/063388 EP2010063388W WO2011032914A1 WO 2011032914 A1 WO2011032914 A1 WO 2011032914A1 EP 2010063388 W EP2010063388 W EP 2010063388W WO 2011032914 A1 WO2011032914 A1 WO 2011032914A1
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Prior art keywords
alkyl
oxygen
silane
hydrogen atoms
catalyst
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PCT/EP2010/063388
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German (de)
English (en)
Inventor
Mathias Matner
Klaus Lorenz
Jörg Hofmann
Michael Ludewig
Axel Schmidt
Frank Kobelka
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Bayer Materialscience Ag
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Publication of WO2011032914A1 publication Critical patent/WO2011032914A1/fr

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    • 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
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
    • 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
    • C08G65/2603—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 the other compounds containing oxygen
    • C08G65/2606—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 the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609—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 the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl 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
    • 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
    • C08G65/2642—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 characterised by the catalyst used
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • C08G65/2663—Metal cyanide catalysts, i.e. DMC's

Definitions

  • the present invention relates to silane-containing polyethers, a process for their preparation and their general use.
  • Silane-terminated polymers have been used commercially for years. In most cases, polyurethane or polyacrylate polymers are converted to the corresponding silane-terminated polymers with the aid of functional silanes. A disadvantage of these polymers is the comparatively high viscosity which is caused by the polymer backbones used.
  • silane-terminated polyethers also have the advantage of lower viscosity compared to the abovementioned silane-terminated polymers.
  • Silane-group-containing polyethers are described in DE-A 1 495 543.
  • the reaction of a polyether with ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane under SnC catalysis is described here.
  • the polyether is first synthesized, and then subsequently reacted with the silane. This is therefore a two-step synthesis, which requires elaborate work-up steps in each step.
  • Polyethers which have hydrolyzable silane groups at both ends are known in principle from, for example, US Pat. No. 3,971,751. It describes a process in which the key intermediate, an olefin-terminated polyether, is prepared by Williamson ether synthesis. Short-chain polyethers prepared by the KOH process are first deprotonated with a suitable base and chain-extended with dichloromethane. Remaining alkoxide groups can then be further reacted with suitable olefin-group-containing alkylating agents, such as allyl chloride, to give the olefin-terminated polyether.
  • suitable olefin-group-containing alkylating agents such as allyl chloride
  • EP-A 0 397 036 discloses a further development of this process by using a double metal cyanide catalyst instead of the KOH process for the preparation of the polyethers.
  • a double metal cyanide catalyst instead of the KOH process for the preparation of the polyethers.
  • the introduction of the double bond continues to succeed only via a Williamson ether synthesis.
  • DE-A 10 2004 006 531 A one-step process is described in DE-A 10 2004 006 531. There, isotactic and thus partially crystalline polymers are synthesized by copolymerization of propylene oxide with functional epoxides when using a special catalyst. Due to the high proportion of crystalline structures, however, these polymers are generally solid at room temperature and can therefore only be used after melting (hot-melt).
  • Example 6 of DE-A 10 2004 006 531 describes e.g.
  • a process for preparing hydrolysable silane-containing polyethers by alkoxylation a. a suitable starter molecule with b. Alkylene oxides c. with compounds having at least one epoxy group and at least one hydrolyzable silane group d.
  • suitable starter molecules having the general structure R 1 XH 2, where X is sulfur or oxygen Oxygen, Zerewitinoff-active hydrogen atoms H are bonded, n can assume values of 2 to 8 and R 1 represents any radical which does not interfere with the alkylene oxide addition reaction, suitable alkylene oxides (b.)
  • R 2 and R 3 independently of one another represent hydrogen, a C 1 -C 4 -alkyl radical or a phenyl radical, where hydrogen atoms and / or methyl groups are preferred and groups R 2 and R 3 bonded to a carbon atom may be identical or different from one another .
  • R 2 and R 3 independently of one another, represent hydrogen, a C 1 -C 4 -alkyl radical or a phenyl radical, hydrogen atoms and / or methyl groups being
  • R 2 and R 3 attached to a C atom may be the same or different
  • [Q] r represents a chain of length r composed of oxygen and carbon atoms, wherein r represents the sum of the carbon and oxygen atoms , where any free valencies are saturated with hydrogen atoms or alkyl radicals, oxygen atoms (peroxide structures) bonded to one another are absent, silicon is always bound to the chain [Q] r via carbon, the chain [Q] r can also be completely oxygen-free, and r values between 1 and 20, R 4 , R 5 and R 6 is either alkyl or O-alkyl, provided that at least one of R 4 , R 5 and R 6 is O-alkyl,
  • catalysts (d.) compounds are used which catalyze the atactic polymerization of 1-alkylene oxides used as racemic mixtures both by basic, acidic and via coordinative mechanisms (d.).
  • DMC double metal cyanide
  • DMC catalysts are known in principle and described in detail in the prior art.
  • Highly active DMC catalysts which are described, for example, in US Pat. No. 5,470,813, are preferably used.
  • a typical example is the highly active DMC catalysts described in EP-A 0 700 949 which, in addition to a double metal cyanide compound (eg zinc hexacyanocobaltate (III)) and an organic complex ligand (eg tert.-butanol), have a number average molecular weight polyether greater than 500 g / mol.
  • a double metal cyanide compound eg zinc hexacyanocobaltate (III)
  • an organic complex ligand eg tert.-butanol
  • basic catalysts such as, for example, alkali metal hydroxides, alkali metal hydrides, alkali metal carboxylates, alkaline earth hydroxides or amines, since these polymerize the atactically atactic at least one of the 1-alkyl epoxides used as the alkylene oxide as racemic mixtures, for example propylene oxide.
  • a disadvantage of these catalysts is their basicity, which may hinder, for example, the curing silane-containing coating resins under the action of moisture. Therefore, it is generally necessary to remove basic traces of catalyst by work-up steps, for example by ion exchange techniques.
  • starter molecules are preferably used compounds having molecular weights of 18 to 10,000 and 2 to 8 Zerewitinoff active hydrogen atoms per molecule.
  • Zerewitinoff-active hydrogen Hydrogen bonded to N, O, or S is termed Zerewitinoff-active hydrogen (sometimes referred to as "active hydrogen") when it reacts with methylmagnesium iodide to yield methane by a method found by Zrewitinoff.
  • active hydrogen Hydrogen bonded to N, O, or S
  • Typical examples of compounds with Zerewitinoff-active hydrogen are compounds containing carboxyl, hydroxyl, amino, imino or thiol groups as functional groups
  • alkylene oxides for example, ethylene oxide, propylene oxide, butylene oxide, styrene or isobutylene oxide can be used. Particularly preferably, ethylene oxide, propylene oxide or butylene oxide are used.
  • the epoxides can be dosed individually as individual substances, successively or in a mixture. If different epoxides are metered in succession, polyether chains with block structures are obtained. Mixed dosage results in mixed block structures.
  • Examples of compounds which have at least one epoxy group and at least one silicon atom carrying hydrolyzable groups are 3- (glycidoxypropyl) trimethoxysilane, 3- (glycidoxypropyl) triethoxysilane and / or 3- (glycidoxypropyl) methyldimethoxysilane, 3- (glycidoxypropyl) methyldiethoxysilane or the corresponding alpha compounds 3- (glycidoxymethyl) trimethoxysilane, 3- (glycidoxymethyl) triethoxysilane and / or the 3- (glycidoxymethyl) methyldimethoxysilane, 3- (glycidoxymethyl) methyldiethoxysilane.
  • epoxysilanes these compounds will be referred to as epoxysilanes.
  • process according to the invention can be carried out according to the following process variants A), B), C):
  • starter The preferably 2 to 8 Zerewitino ff- active hydrogen atoms per molecule containing starter compound (s), hereinafter referred to as "starter” is (are) presented in the reactor.
  • starter the preferably used DMC compounds
  • the OH number of the initiator should not exceed values of 600 mg KOH / g
  • prepolymers having a correspondingly reduced OH number can be prepared from these by basic catalysis by alkylene oxide addition which, after careful separation of basic traces of catalyst, can be used in the process, it is also possible to use mixtures of 2 and more starters.
  • the initiators are then added the alkylene oxide addition catalyst, preferably a DMC compound.
  • basic catalysts such as alkali metal hydroxides, alkali metal hydrides, alkali metal carboxylates, alkaline earth hydroxides or amines are used, it is recommended that the reaction mixture be evacuated and / or stripped with inert gas to remove water. Even when using DMC catalysts, a stripping step should be carried out at the reaction temperature, but at least at 60 ° C., before starting the epoxide dosing.
  • the amounts of catalyst to be used vary in the case of the DMC catalysts preferably to be used between 10 and 1000 ppm. Preferably DMC catalyst amounts between 10 and 300 ppm are used.
  • Basic catalysts are generally used in larger concentrations of 100 to 10,000 ppm. These catalyst concentration data relate based on the total mass of final product in each approach.
  • the reaction temperatures range between 50 ° C and 170 ° C, and preferably between 70 ° C and 160 ° C. During the Epoxiddosierphase the reaction temperatures can also be varied in the specified ranges.
  • the alkylene oxide (s) are now copolymerized together with the epoxysilane (s) on the starter (s).
  • the alkylene oxide (s) and the epoxysilane (s) are metered into the reactor so that the safety-related pressure limits of the system are not exceeded.
  • it may be necessary to activate the catalyst by metering a small amount of epoxide (2 to 10% by weight, based on the mass initially present in the reactor).
  • the activation of a DMC catalyst generally manifests itself by an accelerated pressure drop following an initial pressure rise.
  • the epoxides can be metered in a mixture with each other or in admixture with the epoxysilanes, but it is also possible to meter the epoxies in succession and / or also separated in time from the epoxysilanes.
  • polyether chains are obtained with random monomer units or polyether chains with block structures distributed over the contour length.
  • pure epoxide or epoxide mixture without epoxysilane is preferably metered in to ensure complete conversion of the epoxysilane.
  • the ratio of starters containing Zerewitinoff-active hydrogen atoms to epoxides and epoxysilanes can be varied within wide limits.
  • Possible ranges extend from 0.03 to 5 mol, preferably 0.03 to 1 mol and particularly preferably from 0.03 to 0.25 mol of Zerewitino ff-active hydrogen atoms per kg of product.
  • the ratio of epoxysilane to Zerewitino ff-active hydrogen atoms can also be varied widely. Typical ratios are in the range of 0.5 to 5 moles of epoxy silane per mole of Zerewitinoff active hydrogen atoms, preferred are ratios of 0.5 to 3 moles of epoxy silane per mole of Zerewitinoff active hydrogen atoms.
  • a post-reaction phase is usually followed in which unreacted epoxy groups can react.
  • prepolymers obtained by epoxide addition to (preferably) 2 to 8 Zerewitinoff-active hydrogen atoms per molecule containing starter compounds (initiator compound) can be initially charged; the use of small amounts of the product to be produced is particularly advantageous Product itself.
  • the precursor to be presented as the starting medium is mixed with DMC catalyst amounts as described above before starting the doses and should have a calculated OH number of 5 to 600 mg KOH / g.
  • the amount of starting product to be used advantageously as the starting medium depends on the particular reactor and stirrer geometry as well as the design of the heating and cooling device.
  • the reaction mixture is easy to stir, also the reaction heat should be easily dissipated, or the reactor contents should be slightly heatable.
  • the starter dosing is usually terminated before the end of the epoxide and Epoxysilandostechnik to add to all starter compounds in sufficient amounts of epoxide or epoxysilane and thus to obtain uniform products.
  • the composition of the epoxide / epoxysilane mixture can also be changed, whereby polyether chains with block structures can also be obtained by this process variant.
  • the silane-functional polyethers according to the invention can also be prepared fully continuously by a process as described in WO 98/03571 for the preparation of polyethers.
  • the DMC catalyst in addition to epoxide, epoxysilane and starter (mixture), the DMC catalyst is also fed continuously to the reactor under alkoxylation conditions and the product is taken off continuously after a preselectable mean reactor residence time.
  • Polyether chains with block structures can be obtained in this process variant only by using reactor cascades.
  • the compounds according to the invention are very suitable as binders for the production of elastic adhesives and sealants, preferably for the vehicle construction and construction sector. These adhesives and sealants crosslink under the action of atmospheric moisture via a silanol polycondensation.
  • Another object of the invention are therefore adhesives, sealants, primers and coatings based on the inventive silane-functional polyethers.
  • the silane-functional polyethers according to the invention can be used together with the customary fillers, pigments, plasticizers, drying agents, additives, light stabilizers, antioxidants, thixotropic agents, catalysts, adhesion promoters and optionally further auxiliaries and additives according to known methods of sealant production be formulated.
  • Suitable basic fillers are precipitated or ground chalks, metal oxides, sulfates, silicates, hydroxides, carbonates and bicarbonates.
  • Other fillers are e.g. reinforcing and non-reinforcing fillers such as carbon black, precipitated silicas, fumed silicas, quartz powder or various fibers. Both the basic fillers and the further reinforcing or non-reinforcing fillers may optionally be surface-modified.
  • Particularly suitable as basic fillers are precipitated or ground chalks and fumed silicas. Mixtures of fillers can also be used.
  • plasticizers examples include phthalic acid esters, adipic acid esters, alkylsulfonic acid esters of phenol or phosphoric acid esters. Long-chain hydrocarbons, polyethers and vegetable oils can also be used as plasticizers.
  • thixotropic agents examples include pyrogenic silicic acids, polyamides, hydrogenated castor oil derived products or else polyvinyl chloride.
  • organometallic compounds and amine catalysts which, as is known, promote the silane polycondensation.
  • organometallic compounds are in particular compounds of tin and titanium.
  • Preferred tin compounds are, for example: dibutyltin diacetate, dibutyltin dilaurate, dioctyltin maleate and tin carboxylates such as tin (II) octoate or dibutyltin bis-acetoacetonate.
  • the said tin catalysts may optionally be used in combination with amine catalysts such as aminosilanes or 1,4-diazabicyclo [2.2.2] octane.
  • Preferred titanium compounds are, for example, alkyl titanates, such as diisobutyl bisacete-ethyl ester titanate.
  • Particularly suitable for the sole use of amine catalysts are those which have a particularly high base strength, such as amines with amidine structure.
  • Preferred amine catalysts are For example, l, 8-diazabicyclo [5.4.0] undec-7-ene or 1, 5-diazabicyclo [4.3.0] non-5-ene.
  • protic acids such as, for example, p-toluenesulfonic acid, dodecylbenzenesulfonic acid or other Bronsted acids which are compatible with the particular formulation.
  • protic acids such as, for example, p-toluenesulfonic acid, dodecylbenzenesulfonic acid or other Bronsted acids which are compatible with the particular formulation.
  • a combination of different catalysts is possible.
  • drying agents are alkoxysilyl compounds, such as vinyltrimethoxysilane, methyltrimethoxysilane, isobutyltrimethoxysilane, hexadecyltrimethoxysilane.
  • Adhesion promoters used are the known functional silanes, for example epoxysilanes of the abovementioned type, but also aminosilanes, such as aminopropyltrimethoxysilane, aminopropyltriethoxysilane, N-aminoethyl-3-aminopropyltrimethoxy and / or N-aminoethyl-3-aminopropylmethyldimethoxysilane or also alphasilanes such as aminomethyltrimethoxysilane, aminomethyldimethoxymethylsilane, aminomethyltriethoxysilane, aminomethyldiethoxymethylsilane and / or mercapto silanes.
  • aminosilanes such as aminopropyltrimethoxysilane, aminopropyltriethoxysilane, N-aminoethyl-3-aminopropyltrimethoxy and / or N-aminoethyl-3-aminopropylmethyld
  • Polyol A Polyether diol having an OH number of 56 mg KOH / g, prepared by DMC catalysis by propylene oxide addition to a difunctional starter polyol
  • Polyether triol having an OH number of 56 mg KOH / g, prepared under KOH catalysis by propylene oxide addition to a trifunctional starter
  • Polyol C Polyetherdiol having an OH number of 110 mg KOH / g, prepared under KOH catalysis by propylene oxide addition to a difunctional initiator
  • IRGANOX ® 1076 Octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate (Bayer Materials cience AG, Leverkusen, DE)
  • DMC catalyst was prepared by adding 6 g of propylene oxide activated, which, after a pressure increase of 50 mbar to 0.55 bar, could be detected by an accelerated pressure drop. Then 299.1 g of PO were metered in over 1.72 h at 800 rpm and 130 ° C.
  • plasticizer type Jayflex DIDP from ExxonMobil Chemical
  • precipitation chalk type Socal U1S2 from Solvay
  • adhesion promoter type Dynasylan 1146 from Evonik
  • the product is filled into a commercial polyethylene cartridge and stored at room temperature.

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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)
  • General Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Polyethers (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne des polyéthers comportant des groupes silane, un procédé pour produire ces polyéthers et leur utilisation.
PCT/EP2010/063388 2009-09-18 2010-09-13 Polyéthers comportant des groupes silane WO2011032914A1 (fr)

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DE102009042201.3 2009-09-18
DE200910042201 DE102009042201A1 (de) 2009-09-18 2009-09-18 Silangruppenhaltige Polyether

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2840087A1 (fr) 2013-08-23 2015-02-25 Evonik Degussa GmbH Liaisons contenant des groupes de silicium semi-organiques présentant des groupes de guanidine
CN108083675A (zh) * 2017-12-22 2018-05-29 上海东大化学有限公司 一种宽分布聚羧酸减水剂单体及其制备方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107075105B (zh) 2014-09-23 2019-09-13 科思创德国股份有限公司 含烷氧基甲硅烷基的湿固化聚醚碳酸酯

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EP1146062A1 (fr) * 2000-04-12 2001-10-17 Kaneka Corporation Procédé pour la production de polymères polyoxyalkylène contenant des groupement silyl réticulables
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DE1495543A1 (de) 1963-09-30 1969-02-27 Dow Corning Einkomponentenmassen auf Grundlage silylmodifizierter Polyaether und Verfahren zur Herstellung derselben
US3388079A (en) * 1966-04-26 1968-06-11 Hercules Inc High molecular weight polyethers containing silane groupings
US3971751A (en) 1975-06-09 1976-07-27 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Vulcanizable silylether terminated polymer
JPS5432597A (en) 1977-08-18 1979-03-09 Kanegafuchi Chem Ind Co Ltd Purification of high molecular weight alkylene oxide polymer
JPS58168623A (ja) 1982-03-31 1983-10-05 Kanegafuchi Chem Ind Co Ltd 高分子量アルキレンオキシド重合体の精製法
EP0397036A2 (fr) 1989-05-09 1990-11-14 Asahi Glass Company Ltd. Procédé de production de dérivés d'oxydes de polyalkylènes
US5470813A (en) 1993-11-23 1995-11-28 Arco Chemical Technology, L.P. Double metal cyanide complex catalysts
EP0700949A2 (fr) 1994-09-08 1996-03-13 ARCO Chemical Technology, L.P. Catalyseurs hautement actifs de cyanure de métal de double
US5880245A (en) * 1994-12-27 1999-03-09 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for the preparation of novel reactive silicon group-containing polymer
EP0743093A1 (fr) 1995-05-15 1996-11-20 ARCO Chemical Technology, L.P. Catalyseurs à base de complexe de cyanure métallique double hautement actif
EP0761708A2 (fr) 1995-08-22 1997-03-12 ARCO Chemical Technology, L.P. Compositions contenant des catalyseurs de cyanure de métal double et un polyétherpolyole
WO1997029146A1 (fr) 1996-02-07 1997-08-14 Arco Chemical Technology, L.P. Preparation de polyols catalyses au moyen d'un catalyseur double metal au cyanure impliquant l'addition en continu d'initiateur
WO1997040086A1 (fr) 1996-04-19 1997-10-30 Arco Chemical Technology, L.P. Catalyseurs a haute activite a base de cyanure metallique double
WO1998003571A1 (fr) 1996-07-18 1998-01-29 Arco Chemical Technology, L.P. Preparation en continu de polyols de polyether de polyoxyalkylene a faible insaturation avec addition continuelle d'initiateur
WO1998016310A1 (fr) 1996-10-16 1998-04-23 Arco Chemical Technology, L.P. Catalyseurs a deux cyanures metalliques, contenant des polymeres fonctionnalises
WO2000047649A1 (fr) 1999-02-11 2000-08-17 Bayer Aktiengesellschaft Catalyseurs a base de cyanures metalliques doubles destines a la preparation de polyether-polyols
EP1146062A1 (fr) * 2000-04-12 2001-10-17 Kaneka Corporation Procédé pour la production de polymères polyoxyalkylène contenant des groupement silyl réticulables
WO2005078036A1 (fr) * 2004-02-10 2005-08-25 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Composition de colle a base de copolymeres d'oxyde de polypropylene semi-cristallins et duromeres produits a partir de cette composition
DE102004006531A1 (de) 2004-02-10 2005-09-01 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Teilkristallines Polyether-Copolymer auf Basis von Propylenoxid und daraus herstellbare Duromere

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2840087A1 (fr) 2013-08-23 2015-02-25 Evonik Degussa GmbH Liaisons contenant des groupes de silicium semi-organiques présentant des groupes de guanidine
DE102013216787A1 (de) 2013-08-23 2015-02-26 Evonik Degussa Gmbh Guanidingruppen aufweisende semi-organische Siliciumgruppen enthaltende Verbindungen
CN108083675A (zh) * 2017-12-22 2018-05-29 上海东大化学有限公司 一种宽分布聚羧酸减水剂单体及其制备方法

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