EP2185618A1 - Procédé de production de polyuréthanes dendritiques, hyperramifiés, par extrusion réactive - Google Patents

Procédé de production de polyuréthanes dendritiques, hyperramifiés, par extrusion réactive

Info

Publication number
EP2185618A1
EP2185618A1 EP08787156A EP08787156A EP2185618A1 EP 2185618 A1 EP2185618 A1 EP 2185618A1 EP 08787156 A EP08787156 A EP 08787156A EP 08787156 A EP08787156 A EP 08787156A EP 2185618 A1 EP2185618 A1 EP 2185618A1
Authority
EP
European Patent Office
Prior art keywords
diisocyanate
extruder
intensive
reaction
catalysts
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.)
Withdrawn
Application number
EP08787156A
Other languages
German (de)
English (en)
Inventor
Thomas Weihrauch
Stefan Bernhardt
Matthias Seiler
Kerstin Andres
Markus Schwarz
Silvia Herda
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2185618A1 publication Critical patent/EP2185618A1/fr
Withdrawn legal-status Critical Current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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0895—Manufacture of polymers by continuous processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—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
    • C08G18/70—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
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/25—Component parts, details or accessories; Auxiliary operations
    • B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
    • B29C48/362—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using static mixing devices
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/25—Component parts, details or accessories; Auxiliary operations
    • B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
    • B29C48/395—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders
    • B29C48/40—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders using two or more parallel screws or at least two parallel non-intermeshing screws, e.g. twin screw extruders
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/25—Component parts, details or accessories; Auxiliary operations
    • B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
    • B29C48/395—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders
    • B29C48/40—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders using two or more parallel screws or at least two parallel non-intermeshing screws, e.g. twin screw extruders
    • B29C48/435—Sub-screws
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/25—Component parts, details or accessories; Auxiliary operations
    • B29C48/36—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die
    • B29C48/395—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders
    • B29C48/40—Means for plasticising or homogenising the moulding material or forcing it through the nozzle or die using screws surrounded by a cooperating barrel, e.g. single screw extruders using two or more parallel screws or at least two parallel non-intermeshing screws, e.g. twin screw extruders
    • B29C48/435—Sub-screws
    • B29C48/44—Planetary screws

Definitions

  • the present invention relates to a process for producing hyperbranched, dendritic polyurethanes by means of reactive extrusion.
  • Hyperbranched polymers are already known.
  • EP 1 026 185 A1 discloses a process for the preparation of dendritic or highly branched polyurethanes by reacting diisocyanates and / or polyisocyanates with compounds having at least two isocyanate-reactive groups, wherein at least one of the reactants having functional groups with respect to the other reactants of different reactivity and the Reaction conditions are chosen so that in each reaction step only certain reactive groups react with each other.
  • Preferred isocyanates include aliphatic isocyanates such as isophorone diisocyanate.
  • the compounds having at least two isocyanate-reactive groups are propylene glycol, glycerol, mercaptoethanol, ethanolamine, N-methylethanolamine, diethanolamine, ethanolpropanolamine, dipropanolamine, diisopropanolamine, 2-amino-1, 3-propanediol, 2-amino-2-methyl -1, 3-propanediol and tris (hydroxymethyl) aminomethane mentioned by name.
  • polyurethanes obtainable by the process should serve as crosslinkers for polyurethanes or as building blocks for other polyaddition or polycondensation polymers, as phase mediators, thixotropic agents, nucleating agents or as active ingredient or catalyst carriers.
  • Polyisocyanate polyaddition products comprising
  • reaction ratio being selected so that on average the addition product (A) is an isocyanate group and more than one group reactive with isocyanate groups contains
  • a preferred diisocyanate (b) is isophorone diisocyanate.
  • polyisocyanate polyaddition products obtainable by the process are proposed in particular for the production of paints, coatings, adhesives, sealants, cast elastomers and foams.
  • WO 2004/101624 discloses the preparation of dendritic or hyperbranched polyurethanes by
  • Isophorone diisocyanate to an addition product, wherein the di- or polyols and di- or polyisocyanates are chosen so that the addition product has on average an isocyanate group and more than one hydroxyl group or a hydroxyl group and more than one isocyanate group, 2) reaction of the addition product of step 1) to give a polyaddition product by intermolecular reaction of the hydroxyl groups with the isocyanate groups, it also being possible to react with a compound containing at least two hydroxyl groups, mercapto groups, amino groups or isocyanate groups, 3) optionally reacting the polyaddition product from step 2) with at least two hydroxyl groups, Mercapto, amino or isocyanate group-containing compound.
  • polyaminourethanes obtainable by the process are used as crosslinkers for polyurethane systems or as a building block for other polyaddition or
  • Polycondensation polymers as a phase mediator, as a rheology aid, as a thixotropic agent, as a nucleating reagent or as a drug or catalyst carrier proposed.
  • WO 02/068553 A2 describes a coating composition comprising 1) a carbamate resin with a hyperbranched or star-shaped polyol core, with a first chain piece based on a polycarboxylic acid or a polycarboxylic anhydride, with a second chain piece based on an epoxide and with carbamate groups at the core and / or the second chain piece and 2) a second resin having reactive groups that can react with the carbamate groups of the carbamate resin.
  • the polyol core can be prepared by reacting a first compound containing more than 2 hydroxy groups, such as. 1, 2,6-hexanetriol, with a second compound containing a carboxyl and at least two hydroxy groups.
  • a first compound containing more than 2 hydroxy groups such as. 1, 2,6-hexanetriol
  • the introduction of the carbamate groups can be achieved by reaction with aliphatic or cycloaliphatic diisocyanates. As part of a longer list here u. a. 2,2,4- and 2,4,4-trimethyl-1,6-diisocyanatohexane and isophorone diisocyanate.
  • WO 97/02304 relates to highly functionalized polyurethanes which are composed of molecules with the functional groups A (B) n , where A is an NCO group or an NCO group-reactive group, B is an NCO group or one with an NCO group.
  • A is an NCO group or an NCO group-reactive group
  • B is an NCO group or one with an NCO group.
  • Group reactive group, A is reactive with B and n is a natural number and at least equal to 2.
  • the preparation of the monomer A (B) n can be carried out, for example, starting from isophorone diisocyanate.
  • the invention relates to a process for the solvent-free, continuous production of hyperbranched, dendritic polyurethanes obtained by solvent-free reaction of
  • auxiliaries and additives may be included,
  • End product in particular by rapid cooling.
  • Dendritic polymers are also referred to in the literature as "dendritic polymers.” These dendritic polymers synthesized from multifunctional monomers fall into two distinct categories, the “dendrimers” and the “hyperbranched polymers.” Dendrimers have a very regular, radially symmetric generation structure They are monodisperse globular polymers that are synthesized in multi-step syntheses compared to hyperbranched polymers with high synthetic complexity, characterized by three distinct areas: - the polyfunctional core, which is the center of symmetry, - various well-defined radial-symmetric layers In contrast to the dendrimers, the hyperbranched polymers are polydisperse and irregular in their branching and structure In contrast to dendrimers, in hyperbranched polymers both the tritic and terminal units also have linear units. In each case an example of a dendrimer and a highly branched polymer, constructed from repeating units which each have at least three bonding possibilities, is shown in the following structures:
  • Starting materials for the polyisocanates A are suitable as aromatic di- or polyisocyanates. Particularly suitable are 1, 3 and 1, 4-phenylene diisocyanate, 1, 5-naphthylene diisocyanate, tolidine diisocyanate, 2,6-toluene diisocyanate, 2,4-tolylene diisocyanate (2,4-TDI), 2,4'-diphenylmethane diisocyanate (2,4'-MDI), 4,4'-diphenylmethane diisocyanate, the mixtures of monomeric diphenylmethane diisocyanates (MDI) and oligomeric diphenylmethane diisocyanates (polymer-MDI), xylylene diisocyanate, tetramethylxylylene diisocyanate and triisocyanatotoluene.
  • MDI monomeric diphenylmethane diisocyanates
  • polymer-MDI oligomeric diphen
  • Suitable aliphatic di- or polyisocyanates advantageously have 3 to 16 carbon atoms, preferably 4 to 12 carbon atoms, in the linear or branched alkylene radical and suitable cycloaliphatic or (cyclo) aliphatic diisocyanates advantageously 4 to 18 carbon atoms, preferably 6 to 15 carbon atoms, in the cycloalkylene radical.
  • suitable cycloaliphatic or (cyclo) aliphatic diisocyanates advantageously 4 to 18 carbon atoms, preferably 6 to 15 carbon atoms, in the cycloalkylene radical.
  • (cyclo) aliphatic diisocyanates the skilled worker understands at the same time cyclic and aliphatic bound NCO groups, as z. B. isophorone diisocyanate is the case.
  • cycloaliphatic diisocyanates those which have only directly attached to the cycloaliphatic ring NCO groups, for. B. H 12 MDI.
  • examples are cyclohexane diisocyanate, methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, propylcyclohexane diisocyanate, methyldiethylcyclohexane diisocyanate.
  • IPDI isophorone diisocyanate
  • HDI hexamethylene diisocyanate
  • H12MDI diisocyanatodicyclohexylmethane
  • MPDI 2-methylpentane diisocyanate
  • TMDI 2,2,4-trimethylhexamethylene diisocyanate / 2,4,4-trimethylhexamethylene diisocyanate
  • NBDI norbornane diisocyanate
  • di- and polyisocyanates, isocyanurates and uretdiones can be used.
  • oligoisocyanates or polyisocyanates which are prepared from the abovementioned diisocyanates or polyisocyanates or mixtures thereof by linking by means of urethane, allophanate, urea, biuret, uretdione, amide, isocyanurate, carbodiimide, uretonimine , Oxadiazinthon- or iminooxadiazinedione structures.
  • Particularly suitable are isocyanurates, especially from IPDI and HDI.
  • Suitable compounds B) are all polyols commonly used in PU chemistry, which have at least two alcohol groups of the
  • the monomeric diols are, for example, ethylene glycol,
  • Triethylene glycol butanediol-1, 4, pentanediol-1, 5, hexanediol-1, 6, 3-methylpentanediol
  • the monomeric triols are, for example, trimethylolpropane, dithmethylolpropane, trimethylolethane, hexanthol-1, 2,6, butantol-1, 2,4, tris ( ⁇ -)
  • Hydroxyethyl isocyanurate, pentaerythritol, mannitol or sorbitol.
  • polyols which contain further functional groups (oligomers or polymers). These are the hydroxyl-containing polyesters, polycarbonates, polycaprolactones, polyethers, polythioethers, polyesteramides, polyurethanes or polyacetals known per se. They have a number average molecular weight of 134 to 3,500 g / mol. The polyols are used alone or in mixtures.
  • zinc catalysts such as in particular, for example, zinc 2-ethylhexanolat in butyldiglycol, zinc salts of branched and unbranched fatty acids (C2 - C20), or bismuth catalysts, such as bismuth thneodecanoate in neodecanoic acid. They are used in a concentration of 0.01 to 3 wt .-%.
  • catalysts such as butyltin tris (2-ethylhexanoate) and dibutyltin dilaurate.
  • auxiliaries and additives z.
  • chain terminators As monofunctional isocyanates, chain terminators, blocking agents, chain extenders, degassing agents, stabilizers, other catalysts, flow control agents, inorganic and / or organic pigments and / or fillers, dispersants, wetting agents, defoamers, ionic liquids may be included.
  • the hyperbranched polyurethane prepared according to the invention preferably has a weight-average molecular weight Mw in the range from 1000 g / mol to 200000 g / mol, favorably in the range from 1500 g / mol to 100000 g / mol, particularly preferably in the range from 2000 g / mol to 75000 g / mol, in particular in the range of 2500 g / mol to 50,000 g / mol.
  • the determination of the molecular weight in particular the determination of the weight average molecular weight Mw and the number average molecular weight, can in known manner, for. Example, be measured by gel permeation chromatography (GPC), wherein the measurement is preferably carried out in DMF and as a reference preferred polyethylene glycols Burgath et al in Macromol Chem. Phys., 201 (2000) 782-791). In this case, a calibration curve is advantageously used, which was conveniently obtained using polystyrene standards. These quantities therefore represent apparent measured values.
  • GPC gel permeation chromatography
  • the number average molecular weight can also be determined by steam or membrane osmosis, the z. In K.F. Arndt; G. Müller; Polymer characterization; Hanser Verlag 1996 (steam pressure osmosis) and H. -G. Elias, macromolecules structure synthesis properties, Wegig & Wepf Verlag 1990 (membrane osmosis) are described in more detail.
  • the GPC has proven to be particularly useful according to the invention.
  • the polydispersity Mw / Mn of preferred hyperbranched polyurethanes is preferably in the range of 1 to 50, favorably in the range of 1, 1 to 40, in particular in the range of 1, 2 to 20, preferably to 10.
  • the principle of the process is that the reaction of the starting compounds is carried out continuously, in particular in an extruder, flow tube, intensive kneader, intensive mixer or static mixer by intensive mixing and short-term reaction with heat.
  • the reactants are briefly reacted with heat at temperatures of 25 0 C to 325 0 C, preferably from 50 to 250 0 C, most preferably from 50 to 200 0 C reacted.
  • these residence time and temperature values may also occupy other preferred ranges.
  • a continuous after-reaction is followed.
  • extruders such as single- or multi-screw extruders, in particular twin-screw extruders, planetary roller extruders or ring extruders, flow tubes, intensive kneaders, intensive mixers or static mixers are particularly suitable for the process according to the invention and are preferably used.
  • the cooling of the products may be very important for the molecular design, it may be necessary to change the extruders in the head area, or to use certain nozzle structures. Often it is necessary here to allow a particularly gentle product discharge. This can for example be driven without a top plate.
  • the starting compounds are added to the aggregates usually in separate product streams. If there are more than two product streams, these can also be bundled. Various hydroxyl-containing starting materials can be combined to form a product stream. It is also possible to additionally add catalysts and / or additives such as leveling agents or stabilizers to this product stream. It is likewise possible to combine polyisocyanates and the uretdiones of polyisocyanates with catalysts and / or additives such as leveling agents or stabilizers in a product stream. The material flows can also be divided and thus supplied to the units in different proportions at different locations. In this way, concentration gradients are set deliberately, which can bring about the completeness of the reaction. The entry point of the product streams in the order can be handled variable and time offset. As a result, the structure of the target molecules can be varied.
  • the downstream of the reaction preferably rapid cooling may be integrated in the reaction part, in the form of a multi-housing embodiment as in extruders or Conterna machines.
  • the following can also be used: tube bundles, pipe coils, cooling rolls, cooled chutes, air conveyors, metal conveyor belts and water baths, with and without a downstream granulator.
  • the preparation is first brought to a suitable temperature by further cooling by means of the corresponding aforementioned equipment. Then, the pastillation or crushing into a desired particle size by means of roll crusher, pin mill, hammer mill, shingles, strand granulator (eg., In combination with a cooling medium), other granulators or the like.
  • Example 1 Preparation of a hyperbranched, dendritic polyurethane by the process according to the invention
  • stream 1 consisted of 1, 2,6-hexanetriol.
  • Stream 2 isophorone diisocyanate (IPDI).
  • Stream 3 consisted of the catalyst DBTL. The total amount, relative to the
  • Stream 1 was fed as melt at a rate of 630 g / h in the first housing of a twin-screw extruder (DSE 25) (temperature of the stream 25 0 C).
  • DSE 25 twin-screw extruder
  • Stream 3 was introduced before entering the extruder in stream 2 via a static mixer section (0.78 g / h).
  • the extruder used consisted of 8 housings which could be heated and cooled separately. Housing 1, 2 and 3: 20 - 30 ° C, housing 4: 25-35 0 C, housing 5:
  • housing 6 and 7 150 - 165 0 C
  • housing 8 100 - 105 0 C.
  • the snails were equipped with conveying elements.
  • Screw speed was 250 rpm.
  • the reaction product was immediately cooled after exiting the extruder and discharged on a cooling belt and then ground. It had a content of free NCO groups of 12.1%.

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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)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un procédé de production de polyuréthanes dendritiques, hyperramifiés, par extrusion réactive.
EP08787156A 2007-10-12 2008-08-13 Procédé de production de polyuréthanes dendritiques, hyperramifiés, par extrusion réactive Withdrawn EP2185618A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007049328A DE102007049328A1 (de) 2007-10-12 2007-10-12 Verfahren zur Herstellung hyperverzweigter, dendritischer Polyurethane mittels reaktiver Extrusion
PCT/EP2008/060605 WO2009049941A1 (fr) 2007-10-12 2008-08-13 Procédé de production de polyuréthanes dendritiques, hyperramifiés, par extrusion réactive

Publications (1)

Publication Number Publication Date
EP2185618A1 true EP2185618A1 (fr) 2010-05-19

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EP08787156A Withdrawn EP2185618A1 (fr) 2007-10-12 2008-08-13 Procédé de production de polyuréthanes dendritiques, hyperramifiés, par extrusion réactive

Country Status (5)

Country Link
US (1) US20110065886A1 (fr)
EP (1) EP2185618A1 (fr)
CN (1) CN101407570A (fr)
DE (1) DE102007049328A1 (fr)
WO (1) WO2009049941A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE502006007655D1 (de) 2005-10-25 2010-09-23 Evonik Degussa Gmbh Präparate umfassend hyperverzweigte polymere
DE102011112080A1 (de) 2011-09-03 2013-03-07 Entex Rust & Mitschke Gmbh Einarbeitung von Additiven und Füllstoffen in einem Planetwalzenextruder oder einem Planetwalzenextruderabschnitt
CN102964558B (zh) * 2012-11-22 2015-04-08 中钞油墨有限公司 雕刻凹版油墨用超支化聚合物树脂的合成及其制备工艺
CN102942664A (zh) * 2012-11-28 2013-02-27 安徽大学 一种端羟基超支化聚氨酯的制备方法
CN103865262B (zh) * 2014-03-27 2016-03-23 济南大学 超支化聚合物在防水卷材中的应用
CN105440259B (zh) * 2015-12-16 2018-03-30 陕西科技大学 以异氰脲酸酯为核的超支化水性聚氨酯及其制备方法
CN105778029B (zh) * 2016-03-16 2019-01-04 陕西科技大学 一种超支化聚(异氰脲酸酯-酯)型水性聚氨酯的制备方法
CN115612435B (zh) * 2022-10-20 2023-09-12 唯万科技有限公司 一种密封用耐高温聚氨酯胶及其制备方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0827248A (ja) * 1994-07-15 1996-01-30 Nippon Polyurethane Ind Co Ltd 改質熱可塑性ポリウレタンからなる成形物の製造方法
DE19524045A1 (de) 1995-07-01 1997-01-02 Basf Ag Hochfunktionalisierte Polyurethane
DE19904444A1 (de) 1999-02-04 2000-08-10 Basf Ag Dendrimere und hochverzweigte Polyurethane
DE10030869A1 (de) 2000-06-23 2002-01-03 Basf Ag Mehrfunktionelle Polyisocyanat-Polyadditionsprodukte
GB0019074D0 (en) * 2000-08-03 2000-09-27 Ranier Ltd Precision polyurethane manufacture
US6462144B1 (en) 2000-12-22 2002-10-08 Basf Corporation Carbamate-functional resins and their use in high solids coating compositions
DE10322401A1 (de) 2003-05-16 2004-12-02 Basf Ag Verfahren zur Herstellung von dendrimeren oder hyperverzweigten Polyurethanen
DE102004057430A1 (de) * 2004-11-27 2006-06-01 Degussa Ag Polymere Nano-Kompositwerkstoffe durch kontrollierte Keimbildung von dendritischen Polymeren
DE502006007655D1 (de) * 2005-10-25 2010-09-23 Evonik Degussa Gmbh Präparate umfassend hyperverzweigte polymere
DE102006004077A1 (de) * 2006-01-28 2007-08-02 Degussa Gmbh Verfahren zur Herstellung von hoch reaktiven uretdiongruppenhaltigen Polyurethanverbindungen
DE102006021779A1 (de) * 2006-05-09 2007-11-15 Degussa Gmbh Hyperverzweigte Polyurethane, Verfahren zu ihrer Herstellung sowie ihre Verwendung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009049941A1 *

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DE102007049328A1 (de) 2009-04-16
CN101407570A (zh) 2009-04-15
US20110065886A1 (en) 2011-03-17

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