WO2011067316A1 - Procédé de fabrication d'une dispersion de polymère - Google Patents

Procédé de fabrication d'une dispersion de polymère Download PDF

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Publication number
WO2011067316A1
WO2011067316A1 PCT/EP2010/068698 EP2010068698W WO2011067316A1 WO 2011067316 A1 WO2011067316 A1 WO 2011067316A1 EP 2010068698 W EP2010068698 W EP 2010068698W WO 2011067316 A1 WO2011067316 A1 WO 2011067316A1
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polymer dispersion
ethyl
ionic
dispersion
aqueous
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PCT/EP2010/068698
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German (de)
English (en)
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Uwe Hartnagel
Armin Alteheld
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Basf Se
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Priority to EP10790914A priority Critical patent/EP2507300A1/fr
Publication of WO2011067316A1 publication Critical patent/WO2011067316A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques

Definitions

  • the present invention relates to a process for preparing a dispersion of polymer particles in an ionic liquid (ionic polymer dispersion), which comprises adding and removing an aqueous dispersion of polymer particles (aqueous polymer dispersion) with an ionic liquid the resulting mixture of water is separated.
  • the invention likewise relates to the use of this ionic polymer dispersion in various fields of application, in particular in the field of torque transmission and impact absorption.
  • this ionic polymer dispersion in various fields of application, in particular in the field of torque transmission and impact absorption.
  • the following prior art is assumed.
  • WO 2004/7881 1 discloses the use of ionic liquids in the preparation of block or graft polymers by coupling reactions of the corresponding reactive components.
  • the object of the present invention was to provide a process for the preparation of novel polymer dispersions and the novel polymer dispersions themselves.
  • the object was achieved by the provision of the method defined at the outset.
  • aqueous polymer dispersions are used.
  • Aqueous polymer dispersions are well known. These are fluid systems which contain a disperse phase of dispersed polymer beads as a disperse phase in an aqueous dispersion medium consisting of a plurality of intertwined polymer chains, the so-called polymer particles.
  • the average diameter of the polymer particles is generally in the range from 10 to 1000 nm, often from 50 to 500 nm or from 80 to 300 nm.
  • the polymer solids content of the aqueous polymer dispersions is generally from 10 to 70% by weight.
  • Aqueous polymer dispersions are accessible in particular by free-radically initiated aqueous emulsion polymerization of ethylenically unsaturated monomers. This method has been described many times and is therefore well known to the person skilled in the art [cf. for example, Encyclopedia of Polymer Science and Engineering, Vol. 8, pp. 659-677, John Wiley & Sons, Inc., 1987; DC Blackley, Emulsion Polymerization, pp. 155-465, Applied Science Publishers, Ltd., Essex, 1975; DC Blackley, Polymer Latices, 2nd Edition, Vol. 1, pp. 33-415, Chapman & Hall, 1997; H.
  • the free-radically initiated aqueous emulsion polymerization is usually carried out by dispersing the ethylenically unsaturated monomers, generally with the concomitant use of radical chain transfer agents and dispersing aids, such as emulsifiers and / or protective colloids, in aqueous medium and polymerizing them by means of at least one water-soluble free-radical polymerization initiator.
  • radical chain transfer agents and dispersing aids such as emulsifiers and / or protective colloids
  • the residual contents of unreacted ethylenically unsaturated monomers in the resulting aqueous polymer dispersions are also chemical and / or physical methods known to the person skilled in the art [see, for example, EP-A 771328, DE-A 19624299, DE-A 19621027, DE-A 19741 184, DE-A 19741 187, DE-A 19805122, DE-A 19828183, DE-A 19839199, DE-A 19840586 and 198471 15], the polymerizate solids content is adjusted by dilution or concentration to a desired value or the aqueous polymer dispersion other customary additives, such as, for example, bactericidal, foaming or viscosity-modifying additives, are added.
  • customary additives such as, for example, bactericidal, foaming or viscosity-modifying additives
  • secondary aqueous polymer dispersions are understood to mean those aqueous polymer dispersions whose preparation produces the polymer outside the aqueous dispersing medium, for example in solution of a suitable non-aqueous solvent. This solution is then transferred into the aqueous dispersing medium and the solvent is separated, generally by distillation, with dispersion.
  • Vinyl esters of long-chain fatty acids and / or ethylene in polymerized form are Vinyl esters of long-chain fatty acids and / or ethylene in polymerized form.
  • aqueous polymer dispersions which have dilatant properties are particularly advantageously used according to the invention.
  • dilatant properties when an aqueous polymer dispersion under the action of shear forces has a significant increase in viscosity, without there being a measurable time dependence. That is, dilatant dispersions are characterized by ideally constant shear rate, the so-called critical Shear rate, characterized by a steep increase in shear stress. This described shear thickening is reversible and isothermal.
  • Aqueous polymer dispersions having dilatant properties are described, for example, in EP-A 43464, in particular Examples 1 to 3, EP-A 400416, in particular Examples 1 to 9, DE-A 3433085, in particular Examples A to D and DE-A 19757669, in particular examples 1 to 30, which are to be considered as expressly incorporated herein by reference.
  • preference is given to using those aqueous polymer dispersions whose glass transition temperature is> -90 and ⁇ 180 ° C., in particular> -70 and ⁇ 120 ° C. and advantageously> -20 and ⁇ 90 ° C.
  • glass transition temperature (Tg) is meant the glass transition temperature limit to which it tends to increase in molecular weight according to G.
  • the glass transition temperature is determined by the DSC method (differential scanning calorimetry, 20 K / min, midpoint measurement, DIN 53 765).
  • Tg x1 / Tg1 + x2 / Tg2 + .... xn / Tgn, where x1, x2, .... xn are the mass fractions of the monomers 1, 2, .... n and Tg1, Tg2, .. Tgn the glass transition temperatures of each of only one of the monomers 1, 2, .... n constructed polymers in degrees Kelvin.
  • the Tg values for the homopolymers of most monomers are known and are listed, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th ed., Vol. A21, page 169, Verlag Chemie, Weinheim, 1992; Other sources of glass transition temperatures of homopolymers include, for example, J.
  • the average diameter of the polymer particles present in the aqueous polymer dispersions which can be used according to the invention is generally in the range from 10 to 1000 nm, often 50 to 500 nm or 80 to 300 nm.
  • the solids contents are according to the invention usable aqueous usually> 10 and ⁇ 70 wt .-%, advantageously> 30 and ⁇ 70 wt .-% and particularly advantageously> 40 and ⁇ 60 wt .-%.
  • the aqueous polymer dispersions usable according to the invention contain> 30 and ⁇ 90% by weight, advantageously> 30 and ⁇ 70% by weight and particularly advantageously> 40 and ⁇ 60% by weight of water.
  • the Solids contents or the water contents determined by a defined amount (about 0.8 g) of the aqueous polymer dispersion is dried at 130 ° C to constant weight. From the resulting weight loss, the solids content or the water content can be determined.
  • an ionic liquid is understood as meaning salts (compounds of cations and anions) which at normal pressure (1 atm absolute) have a melting point of less than 200 ° C., preferably less than 150 ° C., more preferably less than 100 ° C., and most preferably own less than 80 ° C.
  • the ionic liquids according to the invention have a melting point> -80 and ⁇ 80 ° C and particularly advantageously> -45 and ⁇ 60 ° C.
  • the ionic liquids are liquid under normal conditions (1 atm absolute, 21 ° C).
  • Preferred ionic liquids contain an organic compound as a cation (organic cation).
  • the ionic liquid may contain other cations, including metal cations, in addition to the organic cation.
  • the cations of particularly preferred ionic liquids are exclusively an organic cation or, in the case of polyvalent anions, a mixture of different organic cations.
  • Suitable organic cations are, in particular, organic compounds containing heteroatoms, such as nitrogen, sulfur, oxygen or phosphorus;
  • the organic cations are compounds having an ammonium group (ammonium cations), an oxonium group (oxonium cations), a sulfonium group (sulfonium cations) or a phosphonium group (phosphonium cations).
  • the organic cation of the ionic liquids are ammonium cations, including non-aromatic compounds having a localized positive charge on the nitrogen atom, for example, tetra-nitrogen (quaternary ammonium) compounds or trivalent nitrogen compounds wherein a bond is a double bond, or aromatic compounds with delocalized positive charge and at least one, preferably one or two nitrogen atoms in the aromatic ring system are understood.
  • Preferred organic cations are quaternary ammonium cations having preferably three or four aliphatic substituents, particularly preferably C 1 to C 12 alkyl groups, on the nitrogen atom, which may optionally be substituted by hydroxyl groups.
  • organic cations containing a heterocyclic ring system having one or two nitrogen atoms as a constituent of the ring system are monocyclic, bicyclic, aromatic or non-aromatic ring systems. Called e.g. bicyclic systems, as described in WO 2008/043837.
  • the bicyclic systems of WO 2008/043837 are diazabicyclo derivatives, preferably of a 7- and a 6-membered ring, which contain an amidinium group; in particular the 1,8,8-diazabicyclo (5.4.0) undec-7-enium cation is mentioned.
  • Very particularly preferred organic cations comprise a five- or six-membered heterocyclic ring system having one or two nitrogen atoms as part of the ring system.
  • Suitable organic cations are pyridinium cations, pyridinium cations, pyrimidinium cations, pyrazinium cations, imidazolium cations, pyrazolium cations, pyrazolinium cations, imidazolinium cations, thiazolium cations, triazolium cations.
  • the nitrogen atoms are in each case by an organic group having generally not more than 20 C-atoms, preferably a hydrocarbon group, in particular a C to Ci6-alkyl group, in particular a C to C10, more preferably a substituted C to C 4 alkyl.
  • the carbon atoms of the ring system can also be substituted by organic groups having generally not more than 20 C atoms, preferably a hydrocarbon group, in particular a C to C 16 -alkyl group, in particular a C to C 10, particularly preferably a C to C 4 -alkyl groups , Particularly preferred ammonium cations are quaternary ammonium cations, imidazolium cations, pyrimidinium cations and pyrazolium cations.
  • the ionic liquids may contain inorganic or organic anions.
  • Such anions are listed, for example, in the above-mentioned WO 03/029329, WO 2007/076979, WO 2006/000197 and WO 2007/128268.
  • Suitable anions are, in particular, those from the group of halides and halogen-containing compounds of the formulas:
  • R a COO the group of borates of the general formulas:
  • R a B0 2 2 , R a R b BO the group of carbonates and carbonic esters of the general formulas:
  • M is a metal and shark is fluorine, chlorine, bromine or iodine
  • r and t are integer positive numbers and indicate the stoichiometry of the complex and s is an integer positive number indicating the charge of the complex
  • v is a whole positive number from 2 to 10; and the group of complex metal ions such as Fe (CN) 6 3 , Fe (CN) 6 4 , MnO 4 , Fe (CO) 4 .
  • R a , R b , R c and R d are each independently
  • Cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, methoxy, ethoxy, formyl, acetyl or Cq F2 (qa) + (1-b) H2a + b with q ⁇ 30, 0 ⁇ a ⁇ q and b 0 or 1 (for example CF 3 , C 2 F 5 , CH 2 CH 2 -C ( q -2) F 2 ( q -2) + i, C 6 Fi 3 , C 8 Fi 7 , C10F21, C12F25); C 3 -C 12 -cycloalkyl and their aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O-substituted components, such as cyclopentyl , 2-methyl-1-cyclopentyl, 3-methyl-1
  • C 2 -C 30 -alkenyl and their aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- or -CO-O-substituted components, such as, for example 2 -Propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or Cq F2 ( q - a ) - (1-b) H2a-b with q ⁇ 30, 0 ⁇ a ⁇ q and b 0 or 1;
  • C 3 -C 12 -cycloalkenyl and their aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O-substituted components, such as 3, for example Cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl or C q F 2 ( q -a) -3 (1-b) H 2 a-3b with q ⁇ 30, 0 ⁇ a ⁇ q and b 0 or 1;
  • R a, R b, R c and R d preferably independently of one another each represent a hydrogen atom or a d- to Ci2-alkyl group.
  • Bis (pentafluoroethylsulfonyl) imide Bis (methylsulfonyl) imide; Bis (p-tolylsulfonyl) imide; Tris (trifluoromethylsulfonyl) methide; Bis (pentafluoroethylsulfonyl) methide; p-tolylsulfonate; tetracarbonylcobaltate; Dimethylenglykolmonomethylethersulfat; oleate; stearate; acrylate; methacrylate; maleate; hydrogen citrate; vinylphosphonate;
  • Bis (pentafluoroethyl) phosphinate such as bis [salicylato (2 -)] borate, bis [oxalato (2-)] borate, bis [1,2-benzenediolato (2 -) - 0,0 '] borate, tetracyano borate, tetrafluoroborate; Dicyanamide; Tris (pentafluoroethyl) trifluorophosphate; Tris (heptafluoropropyl) trifluorophosphate, cyclic aryl phosphates such as catechol phosphate (C6H 4 O 2) P (0) 0 and chlorocobaltate.
  • Borates such as bis [salicylato (2 -)] borate, bis [oxalato (2-)] borate, bis [1,2-benzenediolato (2 -) - 0,0 '] borate, tetracyano borate, tetrafluoroborate; Dicyanamide; Tris (pent
  • Particularly preferred anions are those from the group of alkyl sulfates R a OS0 3 ,
  • R a is a C to C 12 -alkyl group, preferably a C to C 6 -alkyl group, the alkylsulfonates R a S0 3 ,
  • R a is a C 1 to C 12 alkyl group, preferably a C 1 to C 6 alkyl group, of the halgenides, in particular chloride and bromide and the pseudohalides, such as thiocyanate, dicyanamide, the carboxylates R a COO,
  • R a is a C 2 -C 20 -alkyl group, preferably a C 1 -C 4 -alkyl group, in particular acetate, which is phosphates, in particular the dialkyl phosphates of the formula R a R b P0 4 , wherein R a and R b independently of one another represent a C 1 to C 6 alkyl group; in particular, R a and R b are the same alkyl group, which may be mentioned dimethyl phosphate and diethyl phosphate and the phosphonates, especially the Monoalkylphosphonklad.
  • R a R b P03 of the formula R a R b P03, wherein R a and R b independently of one another represent a C 1 - to C 6 -alkyl group.
  • Very particularly preferred anions are chloride, bromide, hydrogensulfate, tetrachloroaluminate, thiocyanate, dicyanamide, methylsulfate, ethylsulfate, methanesulfonate, formate, acetate, dimethyl phosphate, diethyl phosphate, p-tolylsulfonate, tetrafluoroborate and hexafluorophosphate, methylmethylphosphonate and methylphosphonate.
  • Particularly preferred ionic liquids are imidazolium salts of the following formula I:
  • R 1 and R 3 are an organic radical having 1 to 20 C atoms
  • R 2 , R 4 , and R 5 stand for an H atom or an organic radical having 1 to 20 C atoms
  • n 1, 2 or 3.
  • R 1 and R 3 are preferably independently an organic radical having 1 to 10 C atoms.
  • R 1 and R 3 are an aliphatic radical, in particular an aliphatic radical without further heteroatoms, for.
  • an alkyl group Particularly preferably, R 1 and R 3 independently of one another represent a C 1 to C 10 or a C 1 to C 4 alkyl group.
  • R 2 , R 4 and R 5 are preferably independently an H atom or an organic radical having 1 to 10 C atoms. Particularly preferably, R 2 , R 4 and R 5 independently of one another represent an H atom or an alkyl group, in particular R 2 , R 4 and R 5 independently of one another are an H atom or a C 1 - to C 4 -alkyl group. Most preferably, R 2 , R 4 and R 5 are each an H atom.
  • X is an anion, preferably one of the abovementioned anions, more preferably chloride, methanesulfonate, thiocyanate, methylsulfate, ethylsulfate and / or acetate.
  • n is preferably 1.
  • Particularly preferred ionic liquids consist exclusively of an organic cation having one of the above anions.
  • the molecular weight of the ionic liquids is preferably less than 2000 g / mol, more preferably less than 1500 g / mol, more preferably less than 1000 g / mol, and most preferably less than 750 g / mol. In a particular embodiment, the molecular weight is between 100 and 750 g / mol and between 100 and 500 g / mol.
  • the preferred ionic liquid is 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium ethylsufate, 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl 3-methylimidazolium chloride and / or 1 - ethyl-3-methylimidazoliumacetat used.
  • the aqueous dispersion of polymenate per 100 parts by weight of polymer particles> 40 and ⁇ 9900 parts by weight, advantageously> 45 and ⁇ 3000 parts by weight and particularly advantageously> 50 and ⁇ 300 parts by weight of ionic liquid are added.
  • the manner in which the ionic liquid is added to the aqueous polymer dispersion is generally not critical and can be carried out batchwise in one or more portions or continuously with constant or varying flow rates. It is advantageous if the ionic liquid is added to the aqueous polymer dispersion under homogeneous mixing, for example by means of customary stirrers, static and / or dynamic mixing devices.
  • the ionic liquid is chosen so that the ionic liquid and the aqueous polymer dispersion do not influence negatively, for example by coagulation or precipitation of the polymer, which can be tested in doubt by those skilled in the art by means of a few routine experiments.
  • water is added in a manner known to those skilled in the art, for example with continuous mixing, by means of a rotary evaporator, falling film evaporator, freeze-drying apparatus and / or a simple distillation bridge separated, advantageously at a temperature of the mixture in the range> -20 and ⁇ 100 ° C and in particular in the range> 30 and ⁇ 90 ° C.
  • the removal of water advantageously takes place at a pressure ⁇ 1 atm (absolute), with pressures in the range> 0.1 and ⁇ 700 mbar (absolute) or> 10 and ⁇ 500 mbar (absolute) being particularly preferred.
  • the mixture obtained, consisting of the ionic liquid and the aqueous polymer dispersion, according to the invention at least> 50% by weight, advantageously> 70% by weight and in particular advantageously> 90% by weight, of the total amount of water contained in the mixture is removed. Often, the entire amount of water is separated. However, it may be advantageous in embodiments of the invention if not the entire amount of water, but only> 93 and ⁇ 99 wt .-% of the total amount of water is separated. This may be the case, for example, if the pure ionic liquid is not liquid at room temperature. It is essential that small amounts of water greatly reduce the melting temperature of the ionic liquid, so that it is liquid in the desired temperature range.
  • the ionic polymer dispersions according to the invention may additionally contain further customary additives, such as, for example, fillers, for example calcium carbonate, talc, dolomite and precipitated silica, pigments, for example titanium dioxide, pigment dispersants, rheology additives , Preservatives, defoamers and / or biocides.
  • fillers for example calcium carbonate, talc, dolomite and precipitated silica
  • pigments for example titanium dioxide, pigment dispersants, rheology additives , Preservatives, defoamers and / or biocides.
  • the ionic polymer dispersions obtainable according to the invention are mechanically stable and therefore storage-stable for many months. They can be used, for example, for the production of adhesives, sealants, plastic plasters, paper coating slips, fiber webs, coating compositions and impact modifiers, and for the consolidation of sand, textile finishing, leather finishing, or for the modification of mineral binders and plastics.
  • the ionic polymer dispersion obtainable therefrom generally also has dilatant properties.
  • these ionic polymer dispersions with dilatants Properties as a medium for transmitting torques, for example in vibration dampers, speed limiter or hydraulic clutches and shock absorption, for example as a filling in shock absorbers, especially in the automotive industry, but also in sports shoes and hiking boots or as a cushion in ski shoes and as a filling in orthopedic pillows .
  • the ionic polymer dispersions can be used as non-flammable hydraulic fluids, lubricants or cleaning agents.
  • Heating / cooling device 300 g of deionized water were heated to 85 ° C under a nitrogen atmosphere. While stirring, 102 g of feed 1 and 14.0 g of feed 2 were added at this temperature. After 15 minutes, the remaining amounts of feed 1 and feed 2 were fed simultaneously via separate feeds continuously with constant flow rates within two hours to the polymerization mixture.
  • Feed 1 was an aqueous emulsion prepared from 96.3 g of deionized water, 5.6 g of sodium alkyl sulfonate, 37.5 g of ethoxylated isooctylphenol (with an average of 25 ethylene oxide (emulsifier K30 ® from Bayer AG.) Emulsifier 825 ® from BASF SE ), 150 g of methacrylamide, 15.0 g of maleic acid, 488 g of styrene and 225 g of tert-butyl acrylate.
  • Feed 2 was a solution of 135 g of deionized water and 5.3 g of a 7.5% strength by weight aqueous solution of potassium peroxodisulfate.
  • the aqueous polymer dispersion obtained had a solids content of 55% by weight.
  • the average particle diameter was determined to be 210 nm.
  • the solids content was determined by drying a defined amount of the aqueous polymer dispersion (about 0.8 g) with the aid of moisture meter HR73 from Mettler Toledo at a temperature of 130 ° C. to constant weight (about 2 hours). In each case two measurements were carried out. The specified value represents the average of these measurements.
  • the average particle diameter of the polymer particles was determined by dynamic light scattering on a 0.005 to 0.01 weight percent aqueous dispersion at 23 ° C. by means of an Autosizers NC from Malvern Instruments, England. The mean diameter of the cumulant analysis (cumulant zaverage) of the measured autocorrelation function (ISO standard 13321) is given.
  • Example 2 was prepared analogously to Example 1 with the difference that 1-ethyl-3-methylimidazolium methanesulfonate was used instead of 1-ethyl-3-methylimidazolium thiocyanate.
  • Example 3 was prepared analogously to Example 1 with the difference that 1-ethyl-3-methylimidazolium chloride was used instead of 1-ethyl-3-methylimidazolium thiocyanate.
  • Example 4 The preparation of Example 4 was carried out analogously to Example 1 with the difference that 1 - ethyl-3-methylimidazoliumethylsulfat was used instead of 1-ethyl-3-methylimidazoliumthiocyanat.
  • c) Measurement of the Shear Stress The shear stress of the ionic polymer dispersion obtained according to Example 1 was measured as a function of the shear rate and was determined using a shear-voltage controlled rotational viscometer MCR301 from Physica Messrs. engineering GmbH (double gap geometry DG 26.7, measuring body inside radius: 12.33 mm, outside radius: 13.33 mm, inside diameter measuring cup: 1 1, 913 mm, outside radius: 13.796 mm) at 25 ° C.

Abstract

L'invention porte sur un procédé de fabrication d'une dispersion de particules de polymère dans un liquide ionique.
PCT/EP2010/068698 2009-12-04 2010-12-02 Procédé de fabrication d'une dispersion de polymère WO2011067316A1 (fr)

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