WO2011128061A1 - Matières fonctionnalisées et leurs utilisations - Google Patents

Matières fonctionnalisées et leurs utilisations Download PDF

Info

Publication number
WO2011128061A1
WO2011128061A1 PCT/EP2011/001815 EP2011001815W WO2011128061A1 WO 2011128061 A1 WO2011128061 A1 WO 2011128061A1 EP 2011001815 W EP2011001815 W EP 2011001815W WO 2011128061 A1 WO2011128061 A1 WO 2011128061A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
integer
metal
alkyl group
ratio
Prior art date
Application number
PCT/EP2011/001815
Other languages
English (en)
Inventor
John Robert Howe Wilson
Siud Pui Man
Original Assignee
Phosphonics Ltd
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 Phosphonics Ltd filed Critical Phosphonics Ltd
Publication of WO2011128061A1 publication Critical patent/WO2011128061A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B11/00—Obtaining noble metals
    • C22B11/04—Obtaining noble metals by wet processes
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
    • C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
    • C22B3/42—Treatment or purification of solutions, e.g. obtained by leaching by ion-exchange extraction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
    • C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
    • C22B3/22—Treatment or purification of solutions, e.g. obtained by leaching by physical processes, e.g. by filtration, by magnetic means, or by thermal decomposition
    • C22B3/24—Treatment or purification of solutions, e.g. obtained by leaching by physical processes, e.g. by filtration, by magnetic means, or by thermal decomposition by adsorption on solid substances, e.g. by extraction with solid resins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P10/00—Technologies related to metal processing
    • Y02P10/20—Recycling

Definitions

  • the invention relates to functionalised materials and their uses, and in particular a treatment involving a metal scavenger and a process to selectively remove one of more specific metal species from a stream containing a range of metal ions and complexes.
  • Precious metals including platinum, rhodium, palladium, ruthenium, iridium and gold are a limited resource and are used extensively in numerous different applications across a vast array of industries. In addition more and more applications are being found and developed where precious metals are required. Thus there is a growing need to develop or improve systems and processes where the losses of precious metals are minimised. Losses can occur both in their application and in the refining and purification of precious metals. In such cases the precious metal is typically present in either a solid or a liquid. Systems have been developed to manage the former. However recovering precious metals from liquid streams remains a significant challenge given the wide range of formulations and compositions that are used for a diverse range of applications.
  • Functionalised materials are one of several systems that are being developed to remove precious metals from organic and aqueous liquids.
  • a liquid containing one or more precious metals is passed through a material, often described as a metal scavenger, which contains a functional group that possesses an affinity for precious metals.
  • a metal scavenger which contains a functional group that possesses an affinity for precious metals.
  • suitable functionalised materials to remove the desired metal species.
  • precious metals are generally found in the presence of further metal species and in a vast range of different chemical environments. These conditions pose significant technical challenges and improved removal and selectivity to particular metals is desirable.
  • precious metals may be present at low concentrations, for example 0.5 to 2000 ppm along with further metal species at higher concentrations for example 500 to 50,000 ppm.
  • the treatment of these streams with functionalised materials typically results in some initial removal of some of the precious metals present and then the removal of these metals stops.
  • the overall results are very low removal of the desired precious metals from the stream, very low loading of the desired precious metals on the metal scavenger and a very high concentration of the further metal ions on the metal scavenger.
  • Currently a high percentage of these precious metal streams are not being treated in a satisfactory manner or at all and so significant quantities of precious metals are not recovered.
  • their removal from process streams is desirable from an environmental and health perspective or for reasons of quality control, for example in the pharmaceutical industry. New functionalised materials and processes are thus required to improve the capture of these limited and valuable resources.
  • the inventors have devised a treatment involving the use of a functionalised material which has a high and selective affinity for precious metals and a low affinity for further metals along with a periodic washing process that in combination selectively removes the desired precious metal to a high level from a stream containing a high concentration of further metals and complexes for example base and transition metals.
  • the invention provides both a process for treating a feed material comprising a precious metal or a range of precious metals to be removed and further metals or complexes, the further metal species being present in concentrations ranging from 0.3 to 10 s times the combined concentration of the precious metals, the process comprising contacting the feed material and a metal scavenging compound or mixture of compounds to selectively remove the precious metal or metals to be removed from the feed material in the presence of further metals or complexes along with a periodic washing process and optionally a pH adjustment of the feed stream that in combination produces a feed material depleted in the removed precious metal or metals
  • the metal scavenging compounds include functionalised materials and polymers where the framework is an organic polymer such as polystyrene or polyolefin; or an inorganic framework such as silica or alumina, and a functional group is attached to the framework; and the use of a metal scavenging compound or mixtures of said compounds for the recovery of precious metal or metals from a feed
  • X is selected from NRR 2 , NR[(CH 2 ) p NR 1 ]iR 2 , SR, S(CH 2 ) e SR, S(CH 2 ) f U, S[(CH 2 )jS],R, S[(CH 2 ) e S] t (CH 2 ) s Z, NRC(S)NR H, SCH 2 CH(NHR)C0 2 E, SCH2CH(C0 2 E)CH 2 C0 2 E, S(CH 2 )
  • U is a heteroaromatic ring
  • Z is Si0 3 2 or a heteroaromatic ring
  • E is a H, C-MO alkyl or a metal ion M and W is OH, OR, OM or and
  • R, R , R 3 and R 4 are independently selected from hydrogen, C -22 -alkyl group, C 1-22 -aryl group and a C 1-22 -alkylaryl group;
  • R 2 is selected from hydrogen, C -22 -alkyl group, or a C 2 .
  • 10 - alkyl Si(0) 3/2 group, I, s, t and u are independently integers from 1 to 100; i is an integer from 1 to 10,000; m is an integer from 1 to 100; n is an integer from 1 to 100 and e, f, j, p are independently integer from 2 to 20;
  • V is a group which is optionally substituted and selected from a C 1-22 -alkyl group, C 2 . 22 - alkenyl group, a C 2-22 -alkynyl group, an aryl group a C -22 -alkylaryl group, a Ci_ 22 -alkyl group substituted with or containing as part of a chain a sulfide, a sulfoxide, a sulfone, an amine, a polyalkyl amine, a phosphine or other phosphorous containing group; M is a metal ion including base and transition ions; the free valences of the silicate oxygen atoms are saturated by one or more of:
  • a silicon atom of other groups of General Formula A hydrogen, a linear or branched C 1-22 - alkyl group, an end group R 5 3 M 1 0 1/2 , a cross-linking bridge member or by a chain R ⁇ M ⁇ OR ⁇ g Owa or AI(OR 6 ) 3 - h O h/2 or R 5 AI(OR 6 ) 2 . r O r/2 ;
  • M 1 is Si or Ti
  • R 5 and R 6 are independently selected from a linear or branched C 1-22 alkyl group, an aryl group and a C ⁇ -alkylaryl group;
  • k is an integer from 1 to 3
  • q is an integer from 1 to 2
  • h is an integer from 1 to 3;
  • r is an integer from 1 to 2;
  • metal is zirconium, boron, magnesium, iron, nickel or a lanthanide
  • a, b, c and d are integers such that the ratio of b:a is from 0.00001 to 100000 and a and b are always greater than 0 and when c is greater than 0 the ratio of c to a+b is from 0.00001 to 100000 and when d is greater than 0 the ratio of d to a+b is from 0.00001 to 100000.
  • the term "metal" as employed herein includes any species of the metal whether solid metal, a complex or any other form of the metal.
  • the ratio of end group, cross linker or polymer chains to a+b+c+d is from 0 to 999:1 preferably 0.001 to 999:1 and especially 0.01 to 99:1.
  • the removal of the precious metals from the feed material may be due to the precious metals being bound through donor interactions with the functional groups of the metal scavenging compound such as a functionalised polystyrene or polyolefin or a composition of General Formula A, or may be as a result of an ion exchange process.
  • the metal scavenging compound such as a functionalised polystyrene or polyolefin or a composition of General Formula A, or may be as a result of an ion exchange process.
  • the process of the invention is carried out to achieve a pre-determined loading of the desired precious metal or metals on the metal scavenger.
  • the loading of the desired precious metal or metals will be influenced by the available time to treat the feed material. High loadings up to 10% weight are preferred but levels of between 0.4 to 6% weight is acceptable.
  • the feed material may be a continuous stream for example a continuous process reaction feedstock, or may be in the form of a batch of material for discrete treatment.
  • the feed material for example a waste water or a waste process stream or a product stream, may be treated to selectively remove components of the feed material in the presence of similar or higher concentration of other components.
  • the removed component may be a desirable or an undesirable material in the feed material.
  • This process may be used for example in removing desired species such as precious metals from a feed material in a refining or purification process prior to disposal or use of the feed material.
  • the process can also act to provide a desired composition for the feed material that has been depleted in the selectively removed component or components after contact with the metal scavenger.
  • metal scavengers typically comprise a functional group attached to a solid organic or inorganic framework.
  • organic polymer frameworks include polystyrene, polyaromatic or polyolefin resins or fibres.
  • An example of a polyolefin framework is the Smopex® range of metal scavengers.
  • functional groups include carboxylic acids and salts, pyridine, sulfonics acids, amines, sulfides and mercapto containing compounds as well as combination of these functional groups.
  • Preferred compounds of General Formula A include those wherein: X is selected from NRR 2 , NR[(CH 2 ) p NR ]iR 2 , SR, S(CH 2 ) e SR, S[(CH 2 ) j S],R, S[(CH 2 ) e S] t (CH 2 ) s Z, NRC(S)NR 1 H, S(CH 2 ) u C(0)W, S(CH 2 ) j NRC(S)NR 1 H and OCH 2 CH(OH)CH 2 NR[(CH 2 ) p NR 1 ]iR 3 where Z is Si0 3/2 or a heteroaromatic ring and W is NR[(CH 2 ) p NR 1 ]jR 2 .
  • Y is selected from NRR 2 , NR[(CH 2 ) p NR 1 ]iR 2 , SR, S(CH 2 ) e SR, S[(CH 2 ) j S],R, or S[(CH 2 ) e S],(CH 2 ) s Z;
  • R, and R 1 are independently selected from hydrogen, C ⁇ o-alkyl group, Ci_ 22 -aryl group and a C 1-22 -alkylaryl group;
  • R 2 is selected from hydrogen, C 1 -2 2-alkyl group, or a C 2 _i 0 - alkyl Si(0) 3/2 group,
  • R 3 and R 4 are hydrogen;
  • s, t and u are independently integers from 1 to 20;
  • i is an integer from 1 to 10,000;
  • m is an integer from 1 to 10;
  • n is an integer from 1 to 10 and e, j, p are independently integer from 2 to 20.
  • V is a group which is optionally substituted and selected from a C -22 -alkyl group, C 2-22 -alkenyl group, a C 2-22 -alkynyl group, an aryl group a Ci_ 22 -alkylaryl group, a 22 -alkyl group substituted with or containing as part of a chain a sulfide, a sulfoxide, a sulfone, an amine, or a polyalkyl amine.
  • the free valences of the silicate oxygen atoms are saturated by one or more of: a silicon atom of other groups of General Formula A, hydrogen, a linear or branched C 1-10 - alkyl group, an end group R 5 3 M 1 Oi 2 , a cross-linking bridge member or by a chain R 5 q M 1 (OR e ) e Ow2 or AI(OR 6 ) 3 - h O h/2 or R 5 AI(OR 6 ) 2 . r O r/2 ;
  • M 1 is Si or Ti
  • R 5 and R 6 are independently selected from a linear or branched Ci. 2 alkyl group, an aryl group and a C ⁇ o-alkylaryl group;
  • k is an integer from 1 to 3
  • q is an integer from 1 to 2
  • h is an integer from 1 to 3;
  • r is an integer from 1 to 2;
  • metal zirconium, boron, magnesium, iron, nickel or a lanthanide.
  • a, b, c and d are integers such that the ratio of b:a is from 0.00001 to 100 and a and b are always greater than 0 and when c is greater than 0 the ratio of c to a+b is from 0.00001 to 100 and when d is greater than 0 the ratio of d to a+b is from 0.00001 to 00.
  • the composition comprises in combination two or more of these preferred features. In a particularly preferred embodiment, the composition comprises in combination all of these preferred features.
  • the ratio of end group, cross linker or polymer chains to a+b+c+d is from 0 to 999:1 preferably 0.001 to 999:1 and especially 0.01 to 99:1.
  • Particularly preferred compounds of General Formula A include those wherein: X is selected from NRR 2 , NH[(CH 2 ) p NH]iR 2 , SR, S(CH 2 ) e SH, S[(CH 2 ) j S],H, S[(CH 2 ) e S] t (CH 2 ) s Z, NHC(S)NR 1 H, S(CH 2 ) u C(0)W, S(CH 2 ) j NRC(S)NR H and OCH 2 CH(OH)CH 2 NH[(CH 2 ) p NH]iH where Z is Si0 32 or a heteroaromatic ring and W is NH[(CH 2 ) p NH]iH; and when c is greater than 0, Y is selected from NRR 2 , NH[(CH 2 ) p NH]iR 2 , SR, S(CH 2 ) e SH, S[(CH 2 ) j S] t H, or S[(CH 2
  • R and R are independently selected from hydrogen, C 1-10 -alkyl group, C 1-22 -aryl group and a C 1-22 -alkylaryl group;
  • R 2 is selected from hydrogen, d.i 2 -alkyl group, or a C 3 -alkyl Si(0) 3/2 group,
  • R 3 and R 4 are hydrogen;
  • s, t and u are independently integers from 1 to 10;
  • i is an integer from 1 to 10,000;
  • m is an integer from 1 to 5;
  • V is a group which is optionally substituted and selected from a Ci_i 2 -alkyl group, C 2-22 - alkenyl group, a Ci. 22 -alkyl group substituted with or containing as part of a chain a sulfide, or an amine; the free valences of the silicate oxygen atoms are saturated by one or more of:
  • a silicon atom of other groups of General Formula A hydrogen, a linear or branched C 1-10 - alkyl group, an end group R 5 3 M 1 0i 2 , a cross-linking bridge member or by a chain or AI(OR 6 ) 3 . h O h/2 or R 5 AI(OR 6 ) 2 . r O r / 2 ;
  • M 1 is Si
  • R 5 and R 6 are independently selected from a linear or branched C 1-6 alkyl group, and an aryl group;
  • k is an integer from 1 to 3
  • q is an integer from 1 to 2
  • h is an integer from 1 to 3; and r is an integer from 1 to 2;
  • a, b, c and d are integers such that the ratio of b:a is from 0.00001 to 10 and a and b are always greater than 0 and when c is greater than 0 the ratio of c to a+b is from 0.00001 to 10 and when d is greater than 0 the ratio of d to a+b is from 0.00001 to 10.
  • the ratio of end group, cross linker or polymer chains to a+b+c+d is from 0 to 999:1 preferably 0.001 to 999:1 and especially 0.01 to 99:1.
  • the process comprises passing the feed material through a fixed bed containing one or more metal scavengers.
  • the feed material suitably comprises an aqueous solution and may range in pH between 0 and 10.
  • the feed material may comprise an acid, for example hydrochloric acid, nitric acid and sulfuric acid or a mixture of acids.
  • the pH of the feed material may optionally be adjusted using either acid or base to increase the desired metal uptake.
  • the feed material may be passed either up or down through a fixed bed containing a metal scavenger at flow rates suitable for the efficient removal of the desired component.
  • the stream Whilst passing the feed material through a fixed bed of a metal scavenger the stream may be held for a period of time ranging from 1 second to 48 hours so as to ensure effective contact with the desired component to be removed.
  • the fixed bed of a metal scavenger is preferably washed with a suitable compatible solvent to remove the build up of the unwanted ions and complexes around the metal scavenger.
  • the functional group of the metal scavenger possesses a differential affinity, suitably a very high affinity for precious metal as compared to further metals.
  • the flow rate and washing frequency and volume will depend on the volume of feed material to be treated, the nature, combination and concentrations of the precious metals, the concentration of the further metal ions and complexes and the nature of the feed material such as solvent and pH.
  • Flow rate values are preferably from 0.1 to 2000 litres/hour and more preferably 0.1 to 50 litres/hour.
  • the washing volume is suitably from 1 to 1000 Bed Volumes of solvent with desirably 1 to 10 Bed Volumes.
  • the washing frequency preferably is from 30 minutes to 4 days.
  • Suitable washing solvents include water, deionised water, aqueous formulations, alcohols, hydrocarbons, aromatics, and polar solvents.
  • the pH may range from 0-10 with 4-8 preferred.
  • the washing solvent may be passed either up or down through the metal scavenger at flow rates suitable for the efficient removal of the unwanted ions and complexes.
  • the washing solvent may be held in the metal scavenger for a period of time so as to ensure effective washing. The period of time may range from 1 second to 24 hours.
  • the overall process may be conducted at temperatures from 5 to 80°C and pressures up to 10 bar. Preferred temperatures are in the range of 10-60°C.
  • the process also encompasses recycling the feed material through the metal scavenger where necessary or desirable with the aim of removing higher levels of precious metal species as compared to a single pass and loading onto the metal scavenger.
  • a combination of different composition of metal scavengers and in particular of General Formula A may be employed to selectively remove different precious metals for example where different ions, oxidation states and complexes may be present.
  • the invention also encompasses the use of a combination of compositions of metal scavengers to remove a range of specific metals from the feed material.
  • the invention also encompasses the use of a combination of metal scavengers with compositions of General Formula A to remove a range of precious metals species from the feed material.
  • metals such as but not limited to aluminium, iron, copper, bismuth, nickel, selenium and zinc are found or used to aid separation, in similar or higher concentrations than the desired precious metal species.
  • process streams include but not limited to a combined precious metal content of 1-500 ppm along with metal ions such as iron, copper, nickel, aluminium and zinc ranging from 100- 50,000 ppm.
  • Removal of the precious metal species from the feed material may be improved by including a periodic washing step in which a wash liquid is contacted periodically with the metal scavenger including a composition or a mixture of compositions of General Formula A.
  • the washing step is carried out using a ratio of Bed Volume of wash liquid to Bed Volumes of feed material of at least 1 to 100, preferably at least 1 to 80, and desirably at least 1 to 50.
  • the flow rate varied between 14-17 Litres/hour and the washing process involving passing 9 Bed Volumes of deionised water through the material after every 8 hours.
  • the process was conducted at ambient temperature.
  • the average reduction in metal content of the treated stream was platinum - 80%; palladium - 92% and rhodium - 40%.
  • Deionised water 250 mL, 8 Bed Volumes
  • a further 12.5 L of the same solution was passed through the fixed bed at the same flow rate of 0.6 IJh.
  • Samples of the treated stream were taken every 50 mL and metal content was measured by ICP-OES using standard methodology. The average reduction in metal content of the treated solution was platinum - 99%; palladium - 99%, ruthenium - 70% and rhodium - 70%.
  • the flow rate varied between 14-17 LJh and the process was conducted at ambient temperature. After every 8 hour continuous operation the fixed beds were washed with deionised water (20 L, 9 Bed Volumes) at a flow rate of 60 Uh. Samples of the treated feed material were taken every 120 L and metal content was measured by ICP-OES using standard methodology. The average reduction in metal content of the treated solution was platinum - 80%; palladium - 92% and rhodium - 40%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Metallurgy (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Geology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Manufacture And Refinement Of Metals (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne un traitement et une utilisation mettant en jeu un épurateur de métaux, tel qu'une matière organique ou inorganique fonctionnalisée et un procédé pour éliminer sélectivement des ions et complexes métalliques spécifiques à partir d'un courant contenant une gamme d'espèces métalliques dans des concentrations variables.
PCT/EP2011/001815 2010-04-15 2011-04-12 Matières fonctionnalisées et leurs utilisations WO2011128061A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1006368.3 2010-04-15
GBGB1006368.3A GB201006368D0 (en) 2010-04-15 2010-04-15 Functionalised materials and uses thereof

Publications (1)

Publication Number Publication Date
WO2011128061A1 true WO2011128061A1 (fr) 2011-10-20

Family

ID=42245313

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/001815 WO2011128061A1 (fr) 2010-04-15 2011-04-12 Matières fonctionnalisées et leurs utilisations

Country Status (2)

Country Link
GB (1) GB201006368D0 (fr)
WO (1) WO2011128061A1 (fr)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012216972B3 (de) * 2012-09-21 2013-09-19 Hilti Aktiengesellschaft Verwendung oberflächenfunktionalisierter Kieselsäuren als Additiv für Reaktionsharz-Zusammensetzungen sowie dieses enthaltende Harz- und Härter-Zusammensetzungen
WO2014064103A2 (fr) 2012-10-24 2014-05-01 Hilti Aktiengesellschaft Composition de résine de réaction et son utilisation
GB2508350A (en) * 2012-11-28 2014-06-04 Phosphonics Ltd A process for the selective removal of a catalyst from a liquid phase
EP2796433A1 (fr) 2013-04-22 2014-10-29 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
EP2824117A1 (fr) 2013-07-09 2015-01-14 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
EP2824155A1 (fr) 2013-07-09 2015-01-14 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
EP3034520A1 (fr) 2014-12-19 2016-06-22 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
EP3184499A1 (fr) 2015-12-21 2017-06-28 HILTI Aktiengesellschaft Composition de resine reactive, systeme a plusieurs composants et son utilisation
EP3272777A1 (fr) 2016-07-18 2018-01-24 HILTI Aktiengesellschaft Composition de resine reactive a base de methacrylate de sucre et son utilisation
CN108654704A (zh) * 2017-03-31 2018-10-16 湖北硒诺唯新功能化硅胶材料有限公司 一种功能化材料及其生产方法和用途
EP3424971A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane comprenant une résine de réaction, composants de résine de réaction et système de résine de réaction et son utilisation
EP3424968A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane et leur utilisation
EP3424969A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Mélange de composés durcissables par réaction radicalaire et son mélange
EP3424970A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane ramifié et son utilisation
EP3424900A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'époxy et leur utilisation
EP3428208A1 (fr) 2017-07-10 2019-01-16 HILTI Aktiengesellschaft Procédé de préparation d'une composition d'une résine uréthane stable au stockage contenant de tempol
EP3344683A4 (fr) * 2015-08-29 2019-05-29 Si-Novation Ltd Silice modifiée avec des groupes fonctionnels polyorganiques, ses procédés de fabrication et son utilisation
WO2019101883A1 (fr) * 2017-11-22 2019-05-31 Phosphonics Limited Composés fonctionnalisés
EP3587380A1 (fr) 2018-06-27 2020-01-01 HILTI Aktiengesellschaft Utilisation des alkylimidazolidon(méth)acrylates en tant que diluant réactif dans une composition de résine réactive
EP3623407A1 (fr) 2018-09-14 2020-03-18 Hilti Aktiengesellschaft Accélérateur à base d'amines réactif, résine réactive contenant ledit accélérateur ainsi que son utilisation
EP3670612A1 (fr) 2018-12-18 2020-06-24 Hilti Aktiengesellschaft Utilisation de composés de méthacrylate d'uréthane dans des compositions de résine réactive
EP3708591A1 (fr) 2019-03-15 2020-09-16 Hilti Aktiengesellschaft Combinaison d'accélérateur
EP3838863A1 (fr) 2019-12-18 2021-06-23 Hilti Aktiengesellschaft Utilisation d'une composition de résine réactive pour la fixation chimique d'un moyen d'ancrage dans un trou de forage
EP3838862A1 (fr) 2019-12-18 2021-06-23 Hilti Aktiengesellschaft Utilisation d'une composition de résine réactive pour la fixation chimique d'un moyen d'ancrage dans un trou de forage
CN113457629A (zh) * 2020-03-30 2021-10-01 深圳思创环保科技有限公司 一种多胺基复合型净化材料及其制备方法和应用
EP3995525A1 (fr) 2020-11-10 2022-05-11 Hilti Aktiengesellschaft Monomère à deux groupes polymérisables (pour romp et pour polymérisation radicalaire) et son utilisation
EP3995524A1 (fr) 2020-11-10 2022-05-11 Hilti Aktiengesellschaft Système à double cure pour la fixation chimique d'un agent d'ancrage dans un trou foré
EP4056607A1 (fr) 2021-03-12 2022-09-14 Hilti Aktiengesellschaft Mélange de diluant réactif pour la fixation chimique
EP4177229A1 (fr) 2021-11-09 2023-05-10 Hilti Aktiengesellschaft Farine de brique en tant que charge dans les systèmes à composants multiples pour la fixation chimique
EP4177235A1 (fr) 2021-11-09 2023-05-10 HILTI Aktiengesellschaft Matières de recyclage pulvérisées en tant que charges pour systèmes à composants multiples destinées à la fixation chimique
EP4257570A1 (fr) 2022-04-06 2023-10-11 Hilti Aktiengesellschaft Composés à base de composés recyclés pour systèmes de résines réactives à plusieurs composants destinés à la fixation chimique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040251188A1 (en) * 2003-06-10 2004-12-16 Skinner Charles E. Immoblized alkylated amine functional macromolecules, alkylated ammonium salt functional macromolecules, and alkylated quaternary ammonium salt functional macromolecules, process for their preparation and methods for their use
WO2007090676A1 (fr) * 2006-02-10 2007-08-16 Phosphonics Ltd Organopolysiloxanes substitues et leur utilisation
WO2009049911A1 (fr) * 2007-10-20 2009-04-23 Phosphonics Ltd Matériaux fonctionnalisés et utilisations de ceux-ci

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040251188A1 (en) * 2003-06-10 2004-12-16 Skinner Charles E. Immoblized alkylated amine functional macromolecules, alkylated ammonium salt functional macromolecules, and alkylated quaternary ammonium salt functional macromolecules, process for their preparation and methods for their use
WO2007090676A1 (fr) * 2006-02-10 2007-08-16 Phosphonics Ltd Organopolysiloxanes substitues et leur utilisation
WO2009049911A1 (fr) * 2007-10-20 2009-04-23 Phosphonics Ltd Matériaux fonctionnalisés et utilisations de ceux-ci

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
GALAFFU N ET AL: "highly functionlaized sulfur-based silica scavengers for the efficient removal of palladium species from active pharmaceutical ingredients", ORGANIC PROCESS RESEARCH AND DEVELOPMENT, CAMBRIDGE, GB, vol. 11, no. 3, 1 January 2007 (2007-01-01), pages 406 - 413, XP002515248, DOI: DOI:10.1021/OP7000172 *
NICOLA GALAFFU ET AL: "Polymer resin library and the discovery of highly efficient polymer supported reagents and scavengers", MOLECULAR DIVERSITY, KLUWER ACADEMIC PUBLISHERS, DO, vol. 9, no. 4, 1 November 2005 (2005-11-01), pages 263 - 275, XP019258617, ISSN: 1573-501X *
TAVLARIDES L L ET AL: "Sol-Gel Synthesized Adsorbents for Metal Separation", TSINGHUA SCIENCE AND TECHNOLOGY, TSINGHUA UNIVERSITY PRESS, BEIJING, CN, vol. 11, no. 2, 1 April 2006 (2006-04-01), pages 233 - 240, XP022933236, ISSN: 1007-0214, [retrieved on 20060401], DOI: DOI:10.1016/S1007-0214(06)70182-1 *

Cited By (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014044731A1 (fr) 2012-09-21 2014-03-27 Hilti Aktiengesellschaft Utilisation d'acides siliciques fonctionnalisés en surface comme additifs pour des compositions de résine réactive ainsi que compositions de résine et de durcisseur les contenant
DE102012216972B3 (de) * 2012-09-21 2013-09-19 Hilti Aktiengesellschaft Verwendung oberflächenfunktionalisierter Kieselsäuren als Additiv für Reaktionsharz-Zusammensetzungen sowie dieses enthaltende Harz- und Härter-Zusammensetzungen
WO2014064103A2 (fr) 2012-10-24 2014-05-01 Hilti Aktiengesellschaft Composition de résine de réaction et son utilisation
DE102012219479A1 (de) 2012-10-24 2014-05-15 Hilti Aktiengesellschaft Reaktionsharz-Zusammensetzung und deren Verwendung
US10519173B2 (en) 2012-11-28 2019-12-31 Phosphonics Ltd Process for the removal and return of a catalyst to a liquid phase medium
GB2508350A (en) * 2012-11-28 2014-06-04 Phosphonics Ltd A process for the selective removal of a catalyst from a liquid phase
EP2796433A1 (fr) 2013-04-22 2014-10-29 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
EP2824117A1 (fr) 2013-07-09 2015-01-14 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
EP2824155A1 (fr) 2013-07-09 2015-01-14 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
EP3034520A1 (fr) 2014-12-19 2016-06-22 HILTI Aktiengesellschaft Composition de résine réactive et son utilisation
CN110191911A (zh) * 2015-08-29 2019-08-30 湖北硒诺唯新功能化硅胶材料有限公司 有机聚合官能团改性硅胶及其生产工艺与使用
CN110191911B (zh) * 2015-08-29 2021-10-22 湖北硒诺唯新功能化硅胶材料有限公司 有机聚合官能团改性硅胶及其生产工艺与使用
EP3344683A4 (fr) * 2015-08-29 2019-05-29 Si-Novation Ltd Silice modifiée avec des groupes fonctionnels polyorganiques, ses procédés de fabrication et son utilisation
JP7105692B2 (ja) 2015-08-29 2022-07-25 エスアイ－ノベイション リミテッド ポリ有機官能基修飾シリカ、その製造方法、及びその使用
WO2017108553A1 (fr) 2015-12-21 2017-06-29 Hilti Aktiengesellschaft Composition de résine de réaction, système multi-composant et leur utilisation
EP3184499A1 (fr) 2015-12-21 2017-06-28 HILTI Aktiengesellschaft Composition de resine reactive, systeme a plusieurs composants et son utilisation
EP3272777A1 (fr) 2016-07-18 2018-01-24 HILTI Aktiengesellschaft Composition de resine reactive a base de methacrylate de sucre et son utilisation
CN108654704A (zh) * 2017-03-31 2018-10-16 湖北硒诺唯新功能化硅胶材料有限公司 一种功能化材料及其生产方法和用途
CN108654704B (zh) * 2017-03-31 2020-12-01 湖北硒诺唯新功能化硅胶材料有限公司 一种功能化材料及其生产方法和用途
EP3424968A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane et leur utilisation
WO2019007667A1 (fr) 2017-07-03 2019-01-10 Hilti Aktiengesellschaft Composés méthacrylates d'uréthane et leur utilisation
WO2019007725A1 (fr) 2017-07-03 2019-01-10 Hilti Aktiengesellschaft Composés méthacrylates d'uréthane ramifiés et leur utilisation
WO2019007687A1 (fr) 2017-07-03 2019-01-10 Hilti Aktiengesellschaft Mélange de composés durcissables par voie radicalaire et leur utilisation
WO2019007693A1 (fr) 2017-07-03 2019-01-10 Hilti Aktiengesellschaft Résines réactives contenant des composés méthacrylates d'uréthane, constituants constitués de résine réactive ainsi que systèmes à résine réactive et leur utilisation
WO2019007666A1 (fr) 2017-07-03 2019-01-10 Hilti Aktiengesellschaft Composés époxyméthacrylates et leur utilisation
EP3424900A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'époxy et leur utilisation
EP3424970A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane ramifié et son utilisation
EP3424972A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane et leur utilisation
EP3424969A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Mélange de composés durcissables par réaction radicalaire et son mélange
EP3424971A1 (fr) 2017-07-03 2019-01-09 HILTI Aktiengesellschaft Composés de méthacrylate d'uréthane comprenant une résine de réaction, composants de résine de réaction et système de résine de réaction et son utilisation
WO2019011684A1 (fr) 2017-07-10 2019-01-17 Hilti Aktiengesellschaft Procédé de préparation d'une composition de résine uréthane contenant du tempol, qui possède une meilleure stabilité au stockage
EP3428208A1 (fr) 2017-07-10 2019-01-16 HILTI Aktiengesellschaft Procédé de préparation d'une composition d'une résine uréthane stable au stockage contenant de tempol
WO2019101883A1 (fr) * 2017-11-22 2019-05-31 Phosphonics Limited Composés fonctionnalisés
CN111511774A (zh) * 2017-11-22 2020-08-07 磷化有限公司 官能化的化合物
JP2021504556A (ja) * 2017-11-22 2021-02-15 フォスフォニックス リミテッド 官能化化合物
EP3587380A1 (fr) 2018-06-27 2020-01-01 HILTI Aktiengesellschaft Utilisation des alkylimidazolidon(méth)acrylates en tant que diluant réactif dans une composition de résine réactive
WO2020053114A1 (fr) 2018-09-14 2020-03-19 Hilti Aktiengesellschaft Accélérateur à base d'amine réactif, résine réactive contenant celui-ci et leur utilisation
EP3623407A1 (fr) 2018-09-14 2020-03-18 Hilti Aktiengesellschaft Accélérateur à base d'amines réactif, résine réactive contenant ledit accélérateur ainsi que son utilisation
EP3670612A1 (fr) 2018-12-18 2020-06-24 Hilti Aktiengesellschaft Utilisation de composés de méthacrylate d'uréthane dans des compositions de résine réactive
WO2020126369A1 (fr) 2018-12-18 2020-06-25 Hilti Aktiengesellschaft Utilisation de composés uréthane méthacrylate dans des compositions de résine réactive
EP3708591A1 (fr) 2019-03-15 2020-09-16 Hilti Aktiengesellschaft Combinaison d'accélérateur
WO2020187565A1 (fr) 2019-03-15 2020-09-24 Hilti Aktiengesellschaft Combinaison d'accélérateur
EP3838862A1 (fr) 2019-12-18 2021-06-23 Hilti Aktiengesellschaft Utilisation d'une composition de résine réactive pour la fixation chimique d'un moyen d'ancrage dans un trou de forage
EP3838863A1 (fr) 2019-12-18 2021-06-23 Hilti Aktiengesellschaft Utilisation d'une composition de résine réactive pour la fixation chimique d'un moyen d'ancrage dans un trou de forage
CN113457629A (zh) * 2020-03-30 2021-10-01 深圳思创环保科技有限公司 一种多胺基复合型净化材料及其制备方法和应用
EP3995525A1 (fr) 2020-11-10 2022-05-11 Hilti Aktiengesellschaft Monomère à deux groupes polymérisables (pour romp et pour polymérisation radicalaire) et son utilisation
EP3995524A1 (fr) 2020-11-10 2022-05-11 Hilti Aktiengesellschaft Système à double cure pour la fixation chimique d'un agent d'ancrage dans un trou foré
WO2022101025A1 (fr) 2020-11-10 2022-05-19 Hilti Aktiengesellschaft Système à double durcissement pour la fixation chimique de moyens d'ancrage dans un trou de forage
EP4056607A1 (fr) 2021-03-12 2022-09-14 Hilti Aktiengesellschaft Mélange de diluant réactif pour la fixation chimique
EP4177229A1 (fr) 2021-11-09 2023-05-10 Hilti Aktiengesellschaft Farine de brique en tant que charge dans les systèmes à composants multiples pour la fixation chimique
EP4177235A1 (fr) 2021-11-09 2023-05-10 HILTI Aktiengesellschaft Matières de recyclage pulvérisées en tant que charges pour systèmes à composants multiples destinées à la fixation chimique
WO2023083612A1 (fr) 2021-11-09 2023-05-19 Hilti Aktiengesellschaft Poussière de brique utilisée en tant que charge dans des systèmes à composants multiples pour fixation chimique
EP4257570A1 (fr) 2022-04-06 2023-10-11 Hilti Aktiengesellschaft Composés à base de composés recyclés pour systèmes de résines réactives à plusieurs composants destinés à la fixation chimique
WO2023194122A1 (fr) 2022-04-06 2023-10-12 Hilti Aktiengesellschaft Composés à base de composés recyclés, pour des systèmes de résines réactives multicomposants pour fixation chimique

Also Published As

Publication number Publication date
GB201006368D0 (en) 2010-06-02

Similar Documents

Publication Publication Date Title
WO2011128061A1 (fr) Matières fonctionnalisées et leurs utilisations
CN105073643B (zh) 从流体中除去重金属的工艺、方法和系统
UA48156C2 (uk) Спосіб отримання продукту з вуглецю та продукт
NO751650L (fr)
CN105771885A (zh) 一种改性沸石的制备方法及其在含砷废水处理中的应用
EP3296261A1 (fr) Procédé de régénération de résine échangeuse d'ions faiblement basiques
CA2769941C (fr) Une methode pour dissoudre de la dithiazine amorphe
CA2792698C (fr) Procede d'elimination des sels thermostables contenus dans les absorbants de gaz acides
Naveau et al. Organomodification of montmorillonite in supercritical carbon dioxide
JP4423199B2 (ja) ポリスルファンの変換法
JP2017523041A (ja) トリハロメタンで負荷された活性炭のアルカリ加水分解による原位置再生方法
WO2014138908A1 (fr) Procédés pour la régénération d'un absorbant de gaz acide aminé utilisé dans une unité de récupération de gaz acide
CA2412393C (fr) Procede d'extraction du selenium et du mercure de solutions acqueuses
EP2040837B1 (fr) Procédé d'extraction de métaux lourds
TW201433562A (zh) 自烴流移除及回收有機胺類的方法
JP2020164945A (ja) 塩化コバルト水溶液の製造方法
US6156207A (en) Process for the removal of metal compounds from an aqueous acid solution
US20150307434A1 (en) Method for recovering anionic fluorinated emulsifier
EP3271487B1 (fr) Traitement d'oximes dégradés, utilisés comme agents d'extraction de métaux, dans des solutions de traitement organiques
Fukuda et al. Synthesis of NaP1 zeolite from silica waste as an absorbent for the removal of Cs+ and Sr2+ from aqueous solution
JP2014505592A (ja) リン酸セルロース粉末生成物およびその製造方法、ならびに汚染物質を水溶液から除去する用途
JP2013540703A (ja) ジシクロヘキシルジスルフィドの製造方法
JP2016019958A (ja) 非イオン性界面活性剤の精製方法。
CN104918890B (zh) 从包含硫酸盐的水流回收溴化物
CN113457629A (zh) 一种多胺基复合型净化材料及其制备方法和应用

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11717936

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11717936

Country of ref document: EP

Kind code of ref document: A1