EP3116958A2 - Method for treating the surface of particles, the thus obtained particles and use thereof - Google Patents
Method for treating the surface of particles, the thus obtained particles and use thereofInfo
- Publication number
- EP3116958A2 EP3116958A2 EP15716724.8A EP15716724A EP3116958A2 EP 3116958 A2 EP3116958 A2 EP 3116958A2 EP 15716724 A EP15716724 A EP 15716724A EP 3116958 A2 EP3116958 A2 EP 3116958A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- particles
- carbon atoms
- weight
- phthalate
- formula
- 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- Withdrawn
Links
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- 238000010304 firing Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- CGXBXJAUUWZZOP-UHFFFAOYSA-N formaldehyde;phenol;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.OC1=CC=CC=C1.NC1=NC(N)=NC(N)=N1 CGXBXJAUUWZZOP-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 231100000378 teratogenic Toxicity 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
-
- 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
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
- C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/02—Compounds of alkaline earth metals or magnesium
- C09C1/027—Barium sulfates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/04—Compounds of zinc
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/04—Compounds of zinc
- C09C1/06—Lithopone
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3684—Treatment with organo-silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/20—Powder free flowing behaviour
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2237—Oxides; Hydroxides of metals of titanium
- C08K2003/2241—Titanium dioxide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
- C08K2003/3009—Sulfides
- C08K2003/3036—Sulfides of zinc
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
- C08K2003/3045—Sulfates
Definitions
- the present invention relates to surface-treated particles, processes for
- Preparation of the surface-treated particles and their use in particular the surface treatment of titanium dioxide, barium sulfate, zinc sulfide or lithopone particles, and mixtures of these particles with special alkoxylated siloxanes and phthalate-free plasticizers to improve the dispersion in plastics, which are formulated into corresponding polymer compositions divided into the main groups of thermoplastics and thermosets.
- thermoplastics are linear or branched polymers which, in the case of amorphous thermoplastics, above the glass transition temperature (Tg), in the case of (partly) crystalline thermoplastics above the melting temperature (Tm), in principle become flowable. They can be processed in the softened state by molding, extrusion, injection molding or other molding processes to form parts. The chain mobility is so great that the polymer molecules easily slide off each other and the material reaches the molten state (flow area, polymer melt).
- the thermoplastics also include thermoplastically processable plastics with pronounced entropy-elastic properties, the so-called thermoplastic elastomers.
- thermoplastics include all plastics consisting of linear or thermolabelled crosslinked polymer molecules, for example polyolefins, vinyl polymers, polyesters, polyacetals, polyacetates, polycarbonates, in some cases also polyurethanes and ionomers but also TPEs-thermoplastic elastomers (R ⁇ MPP ONLINE, Vers. 3.7, Carlowitz et al Werer, Kunststoffe (Merkness), 1st chapter thermoplastics, Berlin: Springer Verlag (1987), Domininghaus, p. 95 ff).
- Duromers are plastics which are formed by irreversible and close-meshed crosslinking via covalent bonds of oligomers (technically: prepolymers), more rarely of monomers or polymers.
- the term "duromer” is used both for the raw materials before crosslinking (see reaction resins) and as a collective term for the cured, mostly completely amorphous resins
- Duromeres are steel elastic at low temperatures, and they can also be used at higher temperatures , - do not flow viscously, but behave elastically with very limited deformability.
- thermosets include, inter alia, the technically important substance groups of diallyl phthalate resins (DAP), epoxy resins (EP), urea-formaldehyde resins (UF), melamine-formaldehyde resins (MF), melamine-phenol-formaldehyde resins (MPF ), Phenol-Formaldehyde Resins and Unsaturated Polyester Resins (UPES) (R ⁇ MPP ONLINE, Vers 3.7, Becker, GW, Braun, D .; Woebcken, W., Kunststoff-Handbuch, Volume 10: Duroplaste, 2nd Edition, Hanser : Kunststoff, (1988); Elias (6.) 1, 7, 476 ff.).
- DAP diallyl phthalate resins
- EP epoxy resins
- UF urea-formaldehyde resins
- MF melamine-formaldehyde resins
- MPF Phenol-Formaldehyde Resins and Uns
- plasticizers may be added as additives to make the plastics softer, more flexible, smoother and more elastic in use or for further processing.
- Plasticizers may be low-volatile esters, fatty oils, or soft resins.
- the plastics pigments can be added, which are composed of organic or inorganic constituents. For better compatibility, in particular of the inorganic particles, these can be surface-modified.
- Such surface-modified particles may for example consist of an inorganic oxide, which is optionally provided with a further inorganic coating.
- inorganic coating for example a titanium dioxide pigment, silicon oxide and aluminum oxide can serve.
- the inorganic-coated pigment may have an organic coating for influencing the hydrophobicity.
- suitable organic coating compositions include PDMS (polydimethylsiloxanes) or polyalcohols, such as TMP, or substituted siloxanes, such as polydimethylsiloxane alkyl esters, or reactive coupling agents, such as silanes, zirconates or titanates, or phosphorus-containing organic compounds, or steric acid, Ca, Zn, Mg stearates known.
- silicone oils of different chain length / viscosity is known from GB 1 288 581, which can be sprayed on either when grinding the pigment or as an emulsion in a pigment slurry.
- silicone oil surface treatment pigments have good hydrophobicity and, because of their low surface energy, are generally known to be readily incorporated into a low energy plastic environment.
- Such treated pigments have several disadvantages: ⁇ Silicone oil-treated particles have a strong dusting tendency. For example, although titanium dioxide having a relatively high density of 3.9 g / cm 3 should not necessarily tend thereto, the strong dusting tendency after silicone oil treatment is known from US 3,649,321. The tendency to dust is very problematic during further processing and possibly even relevant to safety.
- a low bulk density of the silicone-treated pigments leads to problems when packing the pigment in bagged goods, big bags or silos.
- a high amount of air requires filling with a lower mass per unit pack. If the bagged goods can not be stacked flat on a pallet, the strapping effort or expense increases when the pallets are re-wrapped.
- Automatic packaging with air delivery which are to be regarded as standard with high performance, has this problem in particular.
- Silicone surface treatment oils can lead to further problems in the production of commodities, e.g. lack of recoatability,
- silicone oils or silane-based structures such as methacryloxypropyltrimethoxysilane, are suitable for covering also oxidic surfaces, in order to achieve a hydrophobization or functionalization of the surface and a reduction of the viscosity to allow greater compatibility with the surrounding organic medium and thus a higher efficiency of the pigments used.
- Silanes are sensitive to hydrolysis and generally require an elevated temperature of about 80 ° C to activate the silyl functionality on the pigment or filler surface and to form a polymeric structure on the surface.
- Such defects may be: specks in plastic films that are not only aesthetic nature, but can lead to the formation of holes and leaks in the packaging, specks in the injected plastic part can lead to mechanical defects so cause significantly lower tensile strength or impact resistance and Thus, a high reject rate in the injection molding production or even failure of safety-related components made of plastic in the automotive or electronics sector. , ,
- plasticizers are substances that are added to thermoplastic polymers to make them softer, more flexible and / or more elastic.
- plasticized PVC contains larger amounts of plasticizers and can be easily processed by calendering or extruding.
- the flexibility of the plastic for example a PVC film, can be adjusted in a targeted manner.
- Such films are oxygen and carbon dioxide permeable and have been used for food packaging.
- the phthalate plasticizers used for this use are sometimes said to have teratogenic and fertility-disturbing effects.
- softeners with reduced migration tendency are required. Such plasticizers can then be used for food packaging as well as for medical equipment and children's toys.
- Indispensable requirements for pigments for use in polymers are good flowability and low dusting, good dispersibility and fineness (eg later use in very thin films), fast wettability (to increase throughput in paste production), high possible fill levels (for reduction the storage volume of the stock pastes) and absolute flocculation and settling stability over the period of storage time.
- an approval for the potential indirect contact with food and / or medical compatibility is required.
- Surface treated particles to be used in food grade plastic packaging are subject to European standard EC 10/201 1 and / or US FDA standards.
- pigments There are many requirements for pigments. On the one hand, they have to be optimized with regard to the end use for processing in plastics, on the other hand, the incorporation process into a plasticizer (eg with a dissolver) and its subsequent storage as a paste or liquid as a masterbatch requires a pigment which is suitable for Paints and colors must be optimized. Both requirements can be met in the context of an optimized organic coating. - -
- the object of the invention is therefore to provide particles for plastic products, which meet the aforementioned requirements, especially with regard to the approval of food packaging, and beyond, eliminate the known disadvantages of the prior art. Surprisingly, it has been found that the particles according to the invention having the features according to the main claim solve the problem.
- Such particles which have been post-treated with plasticizers and thus have a coating of plasticizers, are not known in the prior art.
- the invention is therefore directed to particles of Ti0 2 , BaS0 4 , ZnS or lithopone primary particles having a coating with at least one polyether siloxane of the formula (I)
- R 1 is methyl or hydroxy
- Z is a branched or unbranched alkylene radical having 2 to 4
- Carbon atoms preferably 3 carbon atoms
- m is 2 to 4, preferably 3,
- n is 1 to 3, preferably 1 or 2, particularly preferably 1,
- o is 0 or 1, preferably 0, , ,
- EO x , PO y , BO z an oxyalkylene radical containing oxyethylene (EO), oxypropylene (PO) and / or oxybutylene units (BO), wherein x, y and z are> 0 and at least one of x , y and z are not equal to 0,
- R 3 is hydrogen, when n is 1, or a hydrocarbon radical having 1 to 4 carbon atoms,
- a is from 20 to 200, preferably from 30, from 40, from 50, from 60 to 170, to 160, to 150, to 140, to 130, to 120, to 110 and in particular to 70 to 100,
- b is from 1 to 50, preferably from 2, from 3, from 4 to 30, to 25, to 20 and particularly preferably from 5 to 15, with the proviso that when none of the radicals R is R, b is at least 3,
- the at least one phthalate-free plasticizer is present in a proportion of 0.01 to 4.0 wt .-%, preferably 0.05 to 2.0 wt .-%, more preferably 0, 1 to 1, 6 wt .-% .
- the radicals R and R in the formula (I) or R 3 in the formula (II) may each have different meanings if a plurality of radicals R, R and R 3 in a polyethersiloxane of the formula (I) are present.
- R at one end of the molecular chain may have the meaning of methyl and R at the other end of the molecular chain, for example, the meaning of R 1 , which in turn may have a meaning other than one or more R in the side chain when b is a number from 1 to 50 stands.
- R 3 in the polyether radical of the formula (II) in the case of several radicals R in a polyethersiloxane of the formula (I) in each radical R may each have a different meaning.
- the particles of the invention from Ti0 2 , BaS0 4 , ZnS or lithopone primary particles are prepared, which after drying with the polysiloxane compound of formula (I) as above, which are described in DE 102013226800 first described, and the phthalate-free plasticizer be, wherein the coating is formed.
- a coating according to the invention may consist of at least one layer applied to a particle, for example also of two layers. Within a layer, the layer thickness can vary.
- a layer can consist of several components which are regularly or irregularly distributed within the layer, or the components can also be distributed over different layers.
- the at least one layer can cover the surface of a particle in whole or in part.
- the coating according to the invention may preferably comprise a layer which comprises at least one polysiloxane compound of the formula (I) and at least one phthalate-free plasticizer, the two components being randomly distributed within the layer. More preferably, the layer covers the entire particle surface.
- the oxyalkylene group (EO x , PO y , BO z ) may preferably be from 0 to 50% by weight, preferably from 5 to 35% by weight, more preferably from 15 to 30 Wt .-% oxyethylene groups based on the total mass of the radical R have.
- the alkylene radical is a radical according to the invention - (CH 2) 2 4 oxyalkylene group and a radical -0- (CH2) 2- 4 - understood.
- the molar fraction of oxybutylene groups based on the sum of oxypropylene and oxybutylene groups is preferably not more than 50%, preferably up to 45, 40, 35, 30, 25, 20, 15, 10 and in particular up to 5%.
- the numerical proportion of unmodified siloxane fragments with the index a is preferably up to 20 times greater than the proportion of polyether-modified siloxane fragments with the index b, preferably up to 20 times, up to 19, up to 18, up to 17, up to 16 , up to 15, up to 14, up to 13, up to 12, up to 11, up to 10, up to 9, and most preferably up to - - to 8 times.
- the index a is at least 7 times the index b, more preferably at least 8 times, 9 times, 10 times, 1 times, and especially at least 12 times the index b.
- the numerical ratio of index a to index b is preferably 8 to 18, preferably 9 to 15 and particularly preferably 10 to 12.
- the index o is equal to zero.
- the fragment with the index o is preferably an unbranched radical, more preferably an unbranched radical with 3 carbon atoms.
- the fragment with the index o is particularly preferably a glyceryl radical, particularly preferably an n-glyceryl radical, which terminally carries the group -O-Z.
- the radical Z is preferably a linear propylene radical.
- the radical R 3 is preferably a hydrogen.
- particles according to the invention having a coating with at least one compound of the formula (I) where in formula (I):
- R is a polyether radical of formula (II), wherein
- Z is an unbranched alkylene radical having 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms,
- x is 0 to 20, preferably 3 to 15, particularly preferably 4 to 10,
- y is 5 to 100, preferably 8 to 50, particularly preferably 10 to 30,
- z is 0 to 20
- the numerical ratio of index a to index b is preferably 8 to 18, preferably 9 to 15 and particularly preferably 10 to 12.
- the index x is less than or equal to 1, 2 preferably less than 1, 1, more preferably less than 1, less than 0.9, less than 0.8, less than 0.7, less than 0.6, less than 0.5, less than 0, 4; less than 0.3 and in particular less than 0.2. - -
- the index x is preferably between 0.05 and 1.2 times the sum of the indices (y + z), preferably between 0.07 and 0.8 times, in particular between 0.1 and 0.5 times.
- the index z is less than or equal to the index y, preferably less than or equal to the half, the third, the quarter, the fifth, the sixth, the seventh, the eighth, the ninth and in particular less than or equal to one tenth of Indexes y is.
- an oxybutylene group is linear, ie- (CH 2 ) 4-O- and / or branched, ie CH (CH 2 CH 3 ) CH 2 -O-.
- particles according to the invention having a coating with at least one compound of the formula (I) where in formula (I):
- R is methyl
- R 3 is hydrogen
- the particles according to the invention consist of titanium dioxide.
- Polyether siloxanes in the context of the invention are compounds of the formula (I).
- siloxane fragments of the formulas (I) and (II), as well as the siloxane fragments (EO x , PO y , BO z ) and R can be constructed statistically.
- Statistical distributions are blockwise constructed with an arbitrary number of blocks and an arbitrary sequence or a randomized distribution, they can also be constructed alternately or form a gradient over the chain, in particular they can also form all mixed forms in which optionally groups of different Distributions can follow one another. Special designs may cause statistical distributions to be constrained by execution. For all areas that are not affected by the restriction, the statistical distribution does not change.
- the surface-treated particles according to the invention comprise phthalate-free plasticizers.
- Phthalate-free means that the plasticizers according to the invention do not comprise 1, 2-phthalic acid esters.
- Plasticizers which are used to treat the primary particles of TiO 2 , BaSO 4 , ZnS or lithopone for the preparation of the particles according to the invention therefore comprise phthalate-free plasticizers from the group consisting of esters of aliphatic hydrocarbons having 6 to 21 carbon atoms with at least one acid group selected from a carboxyl group -C0 2 H, sulfonyl group -S0 3 H, or sulfinyl group -S0 2 H, with a mono- or polyhydric aliphatic alcohol preferably having six to twenty carbon atoms or a mono- or dihydric aromatic alcohol or mixtures thereof, and esters of aromatic 1,4-para-dicarboxylic acids, preferably 1,4-benzenedicarboxylic acid, or aromatic tricarboxylic acids
- phthalate-free plasticizers are named:
- Esters of aliphatic hydrocarbons having 6 to 21 carbon atoms with at least one acid group selected from a carboxyl group such as esters of polybasic aliphatic carboxylic acids, for example Alkylcarbonklarealkylester or Alkyldicarbonklaredialkylester, Polyethylenglcoldialkylcarbonklar, especially esters of polyhydric cycloaliphatic carboxylic acids, such as esters of cyclohexanedicarboxylic acid, especially esters of 1, 2 cyclohexanedicarboxylic acid; with a monohydric or polyhydric aliphatic alcohol or mixtures thereof;
- At least one acid group selected from a sulfonyl group -SO 3 H, or sulfinyl group -S0 2 H, with a mono- or polyhydric aliphatic or aromatic alcohol or mixtures thereof I; for example
- Aliphatic hydrocarbon having 6 to 21 carbons with at least one
- Acid group in the context of the invention comprises straight-chain, branched or cyclic aliphatic hydrocarbons which may also have one or more substituents.
- Aromatic hydrocarbon such as aromatic 1, 4-dicarboxylic acids or aromatic tricarboxylic acids for the purposes of the invention comprises aromatic C 6 to d 4
- Hydrocarbons which may also have one or more substituents.
- monohydric or polyhydric aliphatic alcohols are meant according to the invention those having six to twenty carbon atoms with one or more hydroxy groups which, as mentioned above, straight-chain, branched or cyclic aliphatic
- Hydrocarbons which may also contain one or more functional groups as mentioned above, may be. These also include oligomers of glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, etc.
- phthalate-free plasticizers 1, 2-dicisononyl cyclohexanedicarboxylate (hexamold dinch-BASF, Elatur CH-Evonik), alkanesulfonic acid phenyl ester, alkanesulfonic acid diphenyl ester (Mesamoll-Lanxess), bis (2-ethylhexyl) 1,4-benzene dicarboxylate (Oxosoft GPO-Oxea) are preferred. , Triethylene glycol bis (2-ethylhexanoate) (Oxosoft 3G8 - Oxea), trioctyl trimellitate (Oxea).
- An advantage of the surface-treated particles according to the invention is the improved dusting tendency compared to prior art pigments, e.g. treated with silicone oil is significantly reduced. This reduces emissions of dust during further processing. Furthermore, possible dust explosions are prevented.
- a further advantage of the particles according to the invention is that they are not subject to any restrictions under current regulations, such as the European standard EC 10/2011 and / or standards of the American FDA, with respect to their use in food packaging.
- a further advantage of the particles and compositions according to the invention is that the pressure filter values are lowered compared to the prior art. This increases the service life of the processing equipment, especially the extruder and reduces their cleaning cycles. - -
- Another advantage of the particles according to the invention is their powder flowability, which is particularly in the discharge of big bags and silo vehicles in the further processing of the particles or in the direct use of the particles in the metering via pneumatic systems and powder screws in the processing unit (eg extruder or kneader) reflected.
- compositions can be formulated in many ways. This manifests itself in that the compositions can be formulated on the basis of thermoplastics, thermosets and plasticizers. This means for the processing industry, such as Paste manufacturers, compounders and masterbatchers have the advantage that the particles according to the invention can be used without further adjustments. This generates a financial advantage and formulation flexibility.
- Another advantage of the particles according to the invention is the low agglomeration tendency due to the coating according to the method of the invention.
- primary particles are to be understood as meaning particles which are obtained as end products from their respective production processes and are thus present as particles of TiO 2 , BaSO 4 , ZnS or lithopone composed of crystallites and / or amorphous units.
- the primary particles for example of TiO 2 , can be subjected to an inorganic pretreatment. These particles can then be treated with the polysiloxanes of formula (I) and plasticizers and subsequently ground. In the milling process and then migrate to the surface of the - -
- titanium dioxide these are, for example, polymorphic forms, rutile, anatase or brookite.
- the titanium dioxide can be prepared by various methods known in the art.
- Various hydrated forms of titanium dioxide can also be used according to the invention.
- titanium dioxide is approved under the name E171 according to food additive regulation 231/2012 / EC, and under the name Cl 77891 according to the cosmetic regulation EC 1223/2009.
- Barium sulfate is used according to the invention under the names barite, baryte, barite white and blanc fixe.
- the different crystal forms of zinc sulfide are used, the alpha-zinc sulfide, known in nature as wurtzite and / or the beta-zinc sulfide, known in nature as zinc blende and sphalerite.
- mixtures of said pigments can also be surface-treated according to the invention.
- the mixtures can be made by mixing the pigments previously prepared in pure form or by co-precipitation, in particular in the form of lithopone.
- these mixtures are primary particles.
- unmodified or inorganically modified titanium dioxide is used. To treat the surface of the Ti0 2 - base body is ground and then covered with one or more layers of inorganic substances.
- the substance to be precipitated is first added in dissolved form. For this purpose, it is necessary to set a pH in the suspension at which the inorganic substance does not precipitate as a solid. From this suspension is then precipitated by a pH change to the neutral point, the inorganic substance.
- the oxides or hydroxides of aluminum, of silicon, of zirconium and also of titanium are used in this treatment (J. Winkler, Titandioxid, (2003), Chapter 3.4, pp. 38-41, ISBN 3-87870-738-X ).
- the surface of the titanium dioxide particles is modified accordingly, so that the particles consist of at most 99 wt .-% of titanium dioxide, preferably at most 95 wt .-%, more preferably at most 85 wt .-% based on the total mass of the particle. Further preferably, the particles are at least 80 wt .-%, preferably at least 85 wt .-%, more preferably at least 90 wt .-% of titanium dioxide based on the total mass of the particles.
- the inorganic titanium dioxide particles are primary particles in the sense of the invention. - -
- Preferred particles are titanium dioxide particles, optionally inorganic modified.
- the surface treatment according to the invention preferably increases the packing density of the particles, which then becomes apparent in a reduced bulk density and also in improved flowability.
- the surface-treated particles according to the invention preferably have a reduced dust tendency.
- the dust tendency can be determined in a so-called dust chamber.
- a defined amount of particles e.g. 100g
- exposed in a downpipe to the free fall in the atmosphere of the environment.
- the particles sediment in the atmosphere at the bottom of a cylinder and a part remains as dust in the gas phase of the drop volume.
- the volume above the sediment is sucked off and the dust collected is filtered off. By weighing the filter, the amount of dust is determined.
- the particles according to the invention preferably have a dust mass of less than 30 mg / 100 g of surface-treated particles, preferably of less than 10 mg / 100 g of surface-treated particles.
- the powder flowability can with a z. B. Ring shear device RST -XS (Schulze, Powder and Bulk Solids, Springer, 2006, Chapter 3.1 .4, page 42).
- the bulk material sample is loaded in a measuring cell from above with a force (normal force) of 3.5 kPa. During the measurement, the shear cell rotates slowly ( ⁇ ). This results in a shear deformation of the bulk material sample. The required force (Fi and F 2 ) is measured. From the ratio of solidification stress ⁇ ⁇ to bulk material strength o c , the flowability ff c of the bulk material is determined. The greater the flowability ff c , the better the bulk material flows.
- the particles according to the invention preferably have a powder flowability of greater than 2.1.
- the determination of the powder flowability can be determined analogously to ASTM D6773-08.
- the dispersibility of the surface-treated particles according to the invention can be determined and evaluated on the basis of the pressure increase in front of a filter (with mesh size to be specified) which is produced when extruding a polymer melt through a sieve packet (pressure filter value).
- the test can z. For example, in accordance with DI N EN 13900-5: 2005. - -
- compositions according to the invention in the form of masterbatches have a pressure filter value (14 ⁇ ) of up to 10 bar * cm 2 / g, more preferably of up to 5 bar * cm 2 / g and in particular of up to 3 bar * cm 2 / g ,
- the pressure filter values can be determined as described in the examples.
- Another way of assessing dispersibility is to determine and evaluate the number of agglomerates in a flat film. Agglomerates are recognizable as specks. The number of specks should be as low as possible.
- Another way of assessing dispersibility is to determine the fineness of the particles of the invention, e.g. in a white paste under defined dispersing conditions.
- a grindometer according to Hegman is suitable for this purpose. The determination may e.g. according to DIN EN 21524 (according to ISO 1525).
- the particles of the invention should be as fine as possible, preferably less than 20 ⁇ , more preferably less than 18 ⁇ , especially less than 16 ⁇ .
- Another object of the invention is the use of the particles according to the invention for the preparation of polymer compositions.
- the particles according to the invention are preferably used for the production of compositions, in particular polymer compositions, containing the particles according to the invention, for processing into plastic moldings or films.
- a further subject of the invention are thus compositions comprising at least one polymer and at least particles according to the invention.
- compositions according to the invention contain, in addition to the particles according to the invention, at least one polymer.
- thermosets are thermoplastics.
- suitable thermosets are unsaturated polyester resins (UP), phenolic resins, melamine resins, formaldehyde molding compounds, vinyl ester resins, diallyl phthalate resins, silicone resins or urea resins.
- thermoplastic materials are, for example, polyethylene, polypropylene, polyester, polyamide, PET, - -
- Polystyrene its copolymers and blends, polycarbonate, PMMA, or polyvinyl chloride suitable.
- thermoplastic compositions according to the invention are preferably processed into masterbatches and / or plastic films.
- compositions are preferably processed into masterbatches, plastic moldings and / or plastic films.
- duromer-containing compositions according to the invention are processed to form plastic molded articles.
- the particles according to the invention can be prepared according to processes of the prior art, but they are preferably prepared by the process described below.
- Another object of the invention is thus a process for the surface treatment of Ti0 2 , BaS0 4 , ZnS or lithopone primary particles, wherein the primary particles with at least one polyether siloxane of the formula (I)
- RR 1 is methyl or hydroxy
- R is a polyether radical of the formula (II):
- Z is a branched or unbranched alkylene radical having 2 to 4 carbon atoms, preferably 3 carbon atoms, - m is 2 to 4, preferably 3,
- n is 1 to 3, preferably 1 or 2, particularly preferably 1,
- o is 0 or 1, preferably 0,
- EO x , PO y , BO z an oxyalkylene radical containing oxyethylene (EO), oxypropylene (PO) and / or oxybutylene units (BO), wherein x, y and z are> 0 and at least one of x , y and z are not equal to 0,
- R 3 is the same or different hydrogen, when n is 1, and one
- Hydrocarbon radical having 1 to 4 carbon atoms, and with the proviso that in R the sum of carbon and oxygen atoms is at least 70,
- a is from 20 to 200, preferably from 30, from 40, from 50, from 60 to 170, to 160, to 150, to 140, to 130, to 120, to 110 and in particular to 70 to 100, b 1 to 50, preferably from 2, from 3, from 4 to 30, to 25, to 20 and particularly preferably 5 to 15, with the proviso that when none of the radicals R is R, b is at least 3,
- the at least one phthalate-free plasticizer in a proportion of 0.01 to 4, 0 wt .-%, preferably 0.05 to 2.0 wt .-%, more preferably 0, 1 to 1, 6 wt .-% is used .
- the data in% by weight being based on the weight of the dried primary particles used.
- the surface treatment of the primary particles can be done dry or wet, in the case of wet execution, this is preferably carried out in emulsion. If the surface treatment is carried out with an emulsified polyethersiloxane of the formula (I), this can be done with the addition of emulsifiers.
- oil-in-water emulsions comprising 5 to 70% by weight of polyethersiloxanes, 1 to 20% by weight of emulsifiers and 20 to 94% by weight of water are preferred.
- Processes for the preparation of silicone emulsions are known to the person skilled in the art. The preparation is usually carried out by stirring all constituents and optionally subsequent homogenization with jet dispersants, rotor-stator or rotor-rotor homogenizers, colloid mills or high-pressure homogenizers. Methods of emulsion preparation are described e.g. in EP0093310, DE2555048, EP1132417. All emulsifiers known to those skilled in the art for preparing polysiloxane emulsions, e.g. anionic, cationic, amphoteric or nonionic emulsifiers.
- anionic emulsifiers are: alkyl sulfates, especially having 8 to 22 carbon atoms in the alkyl group, alkyl and alkylaryl ether sulfates having 8 to 22 carbon atoms in the alkyl group and 1 to 40 oxyethylene or oxypropylene units.
- Sulfonates in particular alkylsulfonates having 8 to 22 carbon atoms, alkylarylsulfonates having 8 to 22 carbon atoms, mono- and diesters of sulfosuccinates, salts of carboxylic acids having 8 to 22 carbon atoms in the alkyl, aryl, alkaryl or arylalkyl unit.
- Phosphoric acid monoesters and diesters and their salts in particular alkyl and alkaryl phosphates having 8 to 22 carbon atoms in the organic moiety, alkyl ether and alkaryl ether phosphates having 8 to 22 carbon atoms in the alkyl or alkaryl moiety and 1 to 40 oxyethylene moieties.
- the counterions may be alkali metal cations, ammonium or protonated substituted amines such as trimethylamine or triethanolamine. Normally, ammonium, sodium and potassium ions are preferred.
- Exemplary, but not limited, cationic emulsifiers are: salts of primary, secondary and tertiary fatty amines having 8 to 24 carbon atoms with acetic acid, sulfuric acid, hydrogen chloride and phosphoric acids. Quaternary alkyl , and alkylphenylammonium salts, especially those having from 6 to 24 carbon atoms, especially their halides, sulfates, phosphates and acetates. Alkylpyridinium, alkylimidazolinium and Alkyloxazoliniumsalze, especially those having an alkyl chain of up to 18 carbon atoms, especially their halides, sulfates, phosphates and acetates.
- Suitable amphoteric emulsifiers are: amino acids with long-chain substituents, e.g. N-alkyldi (aminoethyl) glycine or N-alkyl-2-aminopropionic acid salts.
- Betaines such as e.g. N- (3-acylamidopropyl) -N, N-dimethylammonium salts with an acyl radical of 8 to 20 carbon atoms.
- nonionic emulsifiers are: polyoxyethylene condensates of fatty acids or fatty alcohols having 8 to 22 carbon atoms with up to 95 wt .-% oxyethylene content based on the molecular weight of the emulsifier; Polyoxyethylene derivatives of phenols having 6 to 20 carbon atoms on the aromatic and up to 95 percent oxyethylene content; Oxyethylene condensates of fatty acid monoesters of glycerol having from 10 to 22 carbon atoms and up to 95 percent oxyethylene; Sorbitan esters of fatty acids having from 10 to 22 carbon atoms; Polyoxyethylene sorbitan esters of fatty acids having 10 to 22 carbon atoms; ethoxylated amides, exoxylated amines, alkoxylated polysiloxanes, block copolymers of propylene, ethylene oxide and / or other epoxides.
- the abovementioned fatty structures usually represent the lipophilic part of the emulsifiers.
- a common fatty group is an alkyl group of natural or synthetic origin.
- Known unsaturated groups are the oleyl, linoleyl, decenyl, hexadecenyl and dodecenyl radicals.
- Known saturated groups are lauryl, stearyl, myristyl, palmityl residues.
- Alkyl groups may be cyclic, linear or branched.
- emulsifying an emulsifier or a mixture of several different emulsifiers can be used, wherein preferably at least one nonionic emulsifier, such as ethoxylated fatty acids, ethoxylated linear or branched fatty alcohols, sorbitan fatty acid esters or ethoxylated sorbitan fatty acid esters should be included.
- nonionic emulsifier such as ethoxylated fatty acids, ethoxylated linear or branched fatty alcohols, sorbitan fatty acid esters or ethoxylated sorbitan fatty acid esters should be included.
- known compounds such as polyacrylic acid, polyacrylates, cellulose ethers such as carboxymethylcellulose and hydroxyethylcellulose, natural gums such as xanthan gum, and polyurethanes as well as preservatives and other conventional additives known to those skilled in the art may be added to the emulsions as thickeners.
- the particles can be surface-treated in a one-step or two-step process.
- the mixing and grinding takes place simultaneously.
- the primary particles may be admixed with the polyethersiloxanes of the formula (I) and the phthalate-free plasticizers in the first stage.
- the primary particles may be admixed with the polyethersiloxanes of the formula (I) and the phthalate-free plasticizers in the first stage.
- the primary particles are preferably subsequently or simultaneously mixed and mixed with at least one of the polyethersiloxanes of the formula (I) and at least one phthalate-free plasticizer according to the invention.
- the polyethersiloxanes of the formula (I) and the phthalate-free plasticizers according to the invention are added to the primary particles in succession.
- a ploughshare mixer is used for mixing.
- the first stage is preferably carried out at room temperature or temperatures up to 60 ° C.
- the particles of the first stage are ground.
- Preferred mills are steam jet mills, pin mills, air jet mills, roll mills or ball mill mills, particularly preferred is a steam jet mill.
- the grinding can be carried out at atmospheric pressure or at elevated pressure up to 20 bar, preferably up to 19 bar, 18 bar, 17 bar, 16 bar, 15 bar, 14 bar, 13 bar, 12 bar, 1 1 bar, 10 bar, 9 bar, 8 bar, 7 bar, 6 bar, 5 bar, 4 bar, 3 bar or up to 2 bar.
- up to 20 bar preferably up to 19 bar, 18 bar, 17 bar, 16 bar, 15 bar, 14 bar, 13 bar, 12 bar, 1 1 bar, 10 bar, 9 bar, 8 bar, 7 bar, 6 bar, 5 bar, 4 bar, 3 bar or up to 2 bar.
- the particles are preferably ground in a steam jet mill at a pressure of 8 to 20 bar, preferably 10 to 19 bar, more preferably 12 to 18 bar.
- the particles are preferably surface-treated in a one- or two-stage process.
- the polyethersiloxanes used according to the invention can be prepared by noble metal-catalyzed hydrosilylation of the linear or branched siloxanes of the formula (Ia)
- RR 1 methyl or hydroxy and R is hydrogen, with the abovementioned definitions of the radicals and indices, with terminally unsaturated polyethers, as described for example in EP1520870.
- the hydrosilylating polyethers correspond to the formula (IIa)
- starting alcohols which lead to branched polyethers, which then have two or more oxyalkylene chains, can be used for the preparation of these polyethers.
- Starting alcohols are exemplary, , -
- Trimethylolpropane monoallyl ether or the glycerol monoallyl ethers Preferred according to the invention are glycerol monoallyl ethers, in particular the terminal allylic substituted glycerol monoallyl ether.
- the hydrogen siloxanes used in the preparation of the polyether siloxanes can be prepared as described in the prior art, for example in EP1439200.
- the unsaturated polyethers used can be prepared starting from unsaturated starting alcohols by the methods known in the literature of alkaline alkoxylation or using DMC catalysts as in the prior art, as described for example in DE102007057145.
- compositions refer to the total composition. If mean values are given below, these are, unless stated otherwise, weight average (weight average). If measured values are given below, these values were determined at a pressure of 101325 Pa and a temperature of 25 ° C, unless stated otherwise.
- Figure 1 The figure shows the principle of the dust chamber, whose operation is described in detail in Example 2 in V1.
- the digits mean: 1) case box, 2) release lever, 3) glass cylinder, 4) slider, 5) rubber seal, 6) test tube (filled with quartz cotton), 7) +9) wash bottle (filled with quartz cotton), 8) vacuum pump, - -
- Figure 2 The figure shows the principle of the measuring cell of the ring shear device RST-XS, whose operation is described in detail in Example 2 V2.
- ⁇ rotation of the measuring cell
- Fi and F 2 forces to hold back the lid of the measuring cell
- F N normal force of the lid on the measuring cell.
- the starting material for the dry surface treatment of titanium dioxide was a TiO 2 in rutile modification with an inorganic modification of silica and alumina directly from the spray dryer. This powder was added to the components indicated in Table 1 attached to the end of the description in amounts as indicated and homogenized in a Lödige mixer for 60 seconds. Thereafter, the surface-treated Ti0 2 was ground dry in a steam jet mill with 18 bar steam. Alternatively, the grinding can be done by means of pin mill, air jet mill, roller mill or ball mill. In the following Examples 2-4, investigations were conducted on the samples thus prepared.
- the starting material for the wet surface treatment of Ti0 2 with polyethersiloxanes and phthalate-free plasticizers was a Ti0 2 filter cake after the inorganic modification, wherein the Ti0 2 was present in the rutile modification and the inorganic modification consisted of silica and alumina.
- This filter cake was redispersed in water by means of a dissolver and to the suspension a polyethersiloxane emulsion and phthalate-free plasticizer were added.
- This suspension obtained was spray dried and then the spray grain was ground dry with a steam jet mill with 18 bar steam.
- the starting material for the dry surface treatment of lithopone with polyethersiloxanes was lithopone, which had been produced in a wet-chemical co-precipitation of BaS0 4 and ZnS and which had not yet been dry-ground, ie steam jet-milled.
- This powder was mixed with polyethersiloxane and phthalate-free plasticizers and homogenized in a Lödige mixer for 60 seconds.
- the lithopone wetted with polyethersiloxane and phthalate-free plasticizers was ground dry in a steam jet mill with 10 bar of steam. Alternatively, the grinding can be done by means of pin mill, air jet mill, roller mill or ball mill.
- the powder flowability is determined with the RST -XS ring shear device.
- the bulk material sample is filled into the measuring cell and loaded from above via a lid with a force (normal force) of 3.5 kPa.
- a force normal force
- the shear cell rotates slowly ( ⁇ ).
- the lid is prevented from rotating by means of two tie rods. This results in a shear deformation of the bulk material sample.
- the required force (Fi and F 2 ) is measured. From the ratio of solidification stress ⁇ ⁇ to bulk material strength o c , the flowability ff c of the bulk material is determined. The measurement results are shown in Table 1.
- thermoplastic compositions are also referred to as masterbatches. These masterbatches can be prepared according to the following instructions. - -
- a dry blend of the surface-treated pigments (TiO 2 ) to be investigated and polyethylene as an example of a thermoplastic (LDPE: Lupolen Pureil 1800 SP 15) in a concentration of 50% by weight was prepared by weighing both components in a plastic bottle and then 15 min were mixed on a potholder.
- the resulting dryblend was then added to the Brabender dosing unit and fed via a screw conveyor to the Leistritz DS ZSE 18HP twin-screw extruder for processing. With a speed of 150 revolutions per minute (rpm) and a temperature setting of 150 ° C in all zones, the processing was carried out to masterbatch.
- the polymer strand was granulated.
- compositions containing samples 1-5 were prepared according to Table 1.
- white pastes were prepared.
- DOP dioctyl phthalate
- compositions containing samples 1-5 were prepared according to Table 1.
- the dispersibility was evaluated in a pressure filter test on the basis of the pressure increase in front of the filter, which is produced by extruding a polymer melt through a sieve packet.
- the determination of the pressure filter value was carried out with the single-screw extruder Brabender Plasti-Corder LAB Station (screw diameter: 30 mm / 25D). It was a Siebvers the Fa. GKD with a PZ-Microdur 14 (filter fineness nominally 14 ⁇ ) and a supporting fabric with 315 ⁇ mesh size used. , -
- the extruder was heated to a temperature of 200 ° C.
- the temperature of the filter equipment was set at 230 ° C.
- the filter receiver was installed with the sieve pack.
- the melt stream was passed over the sieve packet and the computer-aided measurement data acquisition was started.
- the measured data were recorded up to a maximum pressure of 150 bar or with a slight increase in pressure up to a duration of 60 minutes.
- the throughput was 40 g / min.
- Table 1 The measurement results are shown in Table 1 below.
- the measure of the dispersion quality is the pressure filter value (DF), which is calculated according to the following formula:
- the samples according to the invention have good dispersibility.
- the examination of the dispersing behavior of pigments in polymers is based on the number of agglomerates in a flat film.
- the masterbatches according to Example 3 (V1) were extruded into films according to the following procedure.
- the masterbatches were diluted with LDPE granules (Pureil PE 3020H) to a concentration of 10% by weight of pigment (TiO 2 ).
- LDPE granules Pureil PE 3020H
- TiO 2 a concentration of 10% by weight of pigment
- the results were graded in a five-step system, with grade 1 no specks, grade 2 scattered specks (there were test areas with 1 to 2 specks but also test areas without specks), grade 3 moderate number of specks (all test areas had specks, average these at less than 5 per test area), Grade 4 many specks (all test areas had 5 to 10 specks) and Grade 5 very many specks (on average, all test areas had at least 10 specks).
- the values in Table 1 below are given as a score of the count of 5 test areas. From Grade 3, the masterbatches are unsuitable for the production of foils.
- the samples according to the invention have good dispersibility.
- the granularity of pigments in a white paste is to be determined under defined dispersing conditions.
- 3 g of the prepared white pastes according to Example 3 (V2) were stirred well in a plastic cup with the same amount of DOP with the spatula.
- the diluted paste was first applied to the Hegman wedge (Grindometer) on the Hegmann wedge from 0 to 100 ⁇ m, and then the correspondingly fine samples were applied to the Hegmann wedge from 0 to 25 ⁇ m (Erichsen).
- the visually determined fineness values in ⁇ were noted and are shown in Table 1 below. A fineness of greater than 20 ⁇ shows a poor dispersion. Table 1
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Application Number | Priority Date | Filing Date | Title |
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DE102014103553 | 2014-03-14 | ||
PCT/DE2015/100105 WO2015135536A2 (en) | 2014-03-14 | 2015-03-13 | Method for treating the surface of particles, the thus obtained particles and use thereof |
Publications (1)
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EP3116958A2 true EP3116958A2 (en) | 2017-01-18 |
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Family Applications (1)
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EP15716724.8A Withdrawn EP3116958A2 (en) | 2014-03-14 | 2015-03-13 | Method for treating the surface of particles, the thus obtained particles and use thereof |
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US (1) | US10131792B2 (en) |
EP (1) | EP3116958A2 (en) |
JP (1) | JP2017519875A (en) |
CN (1) | CN106255729B (en) |
DE (1) | DE102015103697A1 (en) |
TW (1) | TWI558774B (en) |
WO (1) | WO2015135536A2 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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GB201517478D0 (en) | 2015-10-02 | 2015-11-18 | Tioxide Europe Ltd | Particle surface treatment |
EP3187243A1 (en) * | 2015-12-30 | 2017-07-05 | Lhoist Recherche et Développement S.A. | Composition for the purification of flue gas |
EP3187244A1 (en) * | 2015-12-30 | 2017-07-05 | Lhoist Recherche et Développement S.A. | Composition for the purification of flue gas |
TWI617533B (en) | 2016-12-09 | 2018-03-11 | 財團法人工業技術研究院 | Surface-treated ceramic powder and applications thereof |
EP3385337A1 (en) * | 2017-04-05 | 2018-10-10 | Huntsman P&A Uerdingen GmbH | Pigment treated with at least one non-reactive polysiloxane for use in thermoplastics |
CN107216685A (en) * | 2017-06-21 | 2017-09-29 | 嵩县开拓者钼业有限公司 | A kind of preparation method of the dustless molybdenum disulfide of lubricating additive |
EP3425009A1 (en) * | 2017-07-05 | 2019-01-09 | Venator Germany GmbH | Surface modified barium sulfate particles and their use |
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DE3216585C2 (en) | 1982-05-04 | 1984-07-26 | Th. Goldschmidt Ag, 4300 Essen | Process for the production of finely divided, stable O / W emulsions of organopolysiloxanes |
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JP2665951B2 (en) * | 1988-09-27 | 1997-10-22 | 株式会社資生堂 | Solid water-in-oil emulsified cosmetic |
JPH02160709A (en) * | 1988-12-14 | 1990-06-20 | Kao Corp | Water-in-oil type emulsified cosmetic |
DE4140794C1 (en) | 1991-12-11 | 1993-03-11 | Th. Goldschmidt Ag, 4300 Essen, De | |
DE4140793C1 (en) | 1991-12-11 | 1993-03-11 | Th. Goldschmidt Ag, 4300 Essen, De | |
JP3454534B2 (en) * | 1993-03-09 | 2003-10-06 | 水澤化学工業株式会社 | Preparation of granular stabilizers for chlorine-containing polymers. |
JP3384426B2 (en) * | 1994-09-01 | 2003-03-10 | 戸田工業株式会社 | Inorganic colored particle powder, method for producing the same, and water-based paint using the inorganic colored particle powder |
HU216858B (en) * | 1996-03-28 | 1999-09-28 | Csaba Egry | Epoxi resist enamel composition |
JP2000235814A (en) * | 1998-12-14 | 2000-08-29 | Nippon Unicar Co Ltd | Foaming resin composition for manufacturing highly foamed polyethylene covered wire with inert gas foaming method, and highly foamed insulating polyethylene covered wire using the same |
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US7022752B2 (en) * | 2000-09-01 | 2006-04-04 | Toda Kogyo Corporation | Composite particles, process for producing the same, and pigment, paint and resin composition using the same |
DE10301355A1 (en) | 2003-01-16 | 2004-07-29 | Goldschmidt Ag | Equilibration of siloxanes |
DE50302270D1 (en) | 2003-10-04 | 2006-04-13 | Goldschmidt Gmbh | Process for the preparation of organic silicon compounds |
DE102005039398A1 (en) * | 2005-08-20 | 2007-02-22 | Goldschmidt Gmbh | Process for the preparation of addition products of compounds containing SiH groups to olefin-containing reactants in aqueous media |
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DE102009002417A1 (en) * | 2009-04-16 | 2010-10-21 | Evonik Goldschmidt Gmbh | Use of organomodified silicone branched siloxanes for the preparation of cosmetic or pharmaceutical compositions |
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JP2013231134A (en) * | 2012-04-27 | 2013-11-14 | Furukawa Electric Co Ltd:The | Vinyl chloride resin composition, and wire and cable using the same |
DE102013226800A1 (en) * | 2013-12-20 | 2015-06-25 | Evonik Industries Ag | Surface treatment of particles and their use |
-
2015
- 2015-03-12 TW TW104107849A patent/TWI558774B/en not_active IP Right Cessation
- 2015-03-13 US US15/122,655 patent/US10131792B2/en not_active Expired - Fee Related
- 2015-03-13 JP JP2016574333A patent/JP2017519875A/en not_active Ceased
- 2015-03-13 EP EP15716724.8A patent/EP3116958A2/en not_active Withdrawn
- 2015-03-13 DE DE102015103697.5A patent/DE102015103697A1/en not_active Withdrawn
- 2015-03-13 WO PCT/DE2015/100105 patent/WO2015135536A2/en active Application Filing
- 2015-03-13 CN CN201580012818.8A patent/CN106255729B/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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WO2015135536A2 (en) | 2015-09-17 |
DE102015103697A1 (en) | 2015-09-17 |
JP2017519875A (en) | 2017-07-20 |
US20170066924A1 (en) | 2017-03-09 |
TWI558774B (en) | 2016-11-21 |
WO2015135536A3 (en) | 2015-11-05 |
CN106255729B (en) | 2018-05-29 |
CN106255729A (en) | 2016-12-21 |
US10131792B2 (en) | 2018-11-20 |
TW201536874A (en) | 2015-10-01 |
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