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EP4438184A1 - Kollektorzusammensetzung - Google Patents

Kollektorzusammensetzung Download PDF

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Publication number
EP4438184A1
EP4438184A1 EP23164423.8A EP23164423A EP4438184A1 EP 4438184 A1 EP4438184 A1 EP 4438184A1 EP 23164423 A EP23164423 A EP 23164423A EP 4438184 A1 EP4438184 A1 EP 4438184A1
Authority
EP
European Patent Office
Prior art keywords
collector
formula
collector composition
branched
linear
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.)
Pending
Application number
EP23164423.8A
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English (en)
French (fr)
Inventor
Mikhail GOLETS
Magnus Svensson
Jobie JONES
Henrik NORDBERG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nouryon Chemicals International BV
Original Assignee
Nouryon Chemicals International BV
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 Nouryon Chemicals International BV filed Critical Nouryon Chemicals International BV
Priority to EP23164423.8A priority Critical patent/EP4438184A1/de
Publication of EP4438184A1 publication Critical patent/EP4438184A1/de
Pending legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/012—Organic compounds containing sulfur
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/01—Organic compounds containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/01—Organic compounds containing nitrogen
    • B03D1/011—Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D2201/00—Specified effects produced by the flotation agents
    • B03D2201/02—Collectors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D2203/00—Specified materials treated by the flotation agents; Specified applications
    • B03D2203/02—Ores

Definitions

  • the present disclosure relates to collector compositions comprising at least one bis-dithiocarbamate compound as defined herein and the use of said collector compositions in mineral flotation methods.
  • Froth flotation is a physico-chemical process used to separate mineral particles considered economically valuable from those considered waste. It is based on the ability of air bubbles to selectively attach to those particles that were previously rendered hydrophobic. The particle-bubble combinations then rise to the froth phase from where the flotation cell is discharged, whilst the hydrophilic particles remain in the flotation cell. Particle hydrophobicity is, in turn, induced by special chemicals called collectors. In direct flotation systems, it is the economically valuable minerals which are rendered hydrophobic by the action of the collector. Similarly, in reverse flotation systems, the collector renders hydrophobicity to those mineral particles considered waste.
  • Frothers are well-known class of reagents used in mineral flotation. Commonly, the frother is added in a step after the pulp ore was conditioned with the collector. Frothers help optimize and control such important froth characteristics as volume (height) and stability.
  • Recovery refers to the percentage of valuable product contained in the ore that is removed into the concentrate stream after flotation.
  • Grade refers to the percentage of the economically valuable product in the concentrate after flotation. A higher value of recovery or grade indicates a more efficient flotation system.
  • xanthates are good collectors for metallic sulphides (flotation agents known as "collectors” are generally used to facilitate the separation of a particular ore).
  • Methyl isobutyl carbinol (MIBC) is the most commonly used frother in flotation of sulfide minerals.
  • frothers are also used.
  • MIBC Methyl isobutyl carbinol
  • CA771181 discloses dithiocarbamate derivatives of bis-hexamethylene triamine as potential alternatives to standard xanthate collectors in the recovery of copper from copper ore. The xanthates appeared to outperform the dithiocarbamate derivatives in terms of copper recovery.
  • US4702821 and US4554068 disclose carboxyalkyl dithiocarbamate salts for suppressing Cu, Fe, and Pb in the flotation of Mo.
  • US20080185317 discloses novel N-alkoxycarbonyl S-alkyl dithiocarbamates collector compounds useful in the flotation of a number of valuable metals.
  • collector compounds have been found to not only improve recovery for a range of metals, but also improve sulfur recovery at the same time. As shown in the worked examples, these collector compounds outperform the standard xanthates in both aspects.
  • the present disclosure relates to a collector composition
  • a collector composition comprising at least one bis-dithiocarbamate compound of formula (I): wherein:
  • R 1 is H or a cationic counterion, and more preferably R 1 is a cationic counterion.
  • R 1 may be any suitable cationic counterion that is capable of forming a stable salt with the dithiocarbamate moiety.
  • Preferred cationic counterions include, but are not limited to, alkali(ne) metal cations, such as Li + , Na + , K + , Mg 2+ , Ca 2+ , and ammonium cations, such as those of the formula NR 1 R 2 R 3 R 4 , wherein each of R 1 , R 2 , R 3 , and R 4 is independently selected from H or C 1 -C 12 alkyl.
  • R 2 is a C12-C20 linear or branched, saturated or unsaturated alkyl, most preferably a C12-C18 linear or branched, saturated or unsaturated alkyl.
  • These fatty compounds may originate from a renewable natural source, such as, but not limited to, coconut oil or tallow.
  • y is an integer from 2-6, preferably from 2-4, and most preferably y is 3.
  • the bis-dithiocarbamate compound of formula (I) is wherein:
  • the collector composition may contain the at least one bis-dithiocarbamate compound of formula (I) in an amount of from 1-100% relative to the total weight of the collector composition, preferably in an amount of at least 5 wt.%.
  • the collector composition may be in the form of an aqueous or aqueous-alcoholic composition comprising from 5-50 wt.%, preferably from 10-45 wt.%, preferably from 15-40 wt.% of the bis-dithiocarbamate compound of formula (I).
  • Certain impurities may also be present in the collector composition, such as the monoamine dithiocarbamate or the mono-substituted dithiocarbamate: [R 1 , R 2 and y are as defined above]
  • the impurities originate from the synthesis of the compounds of formula (I) and are typically present in a total amount of less than 15 wt.% relative to the amount of the at least one compound of formula (I). If desired, these impurities can be removed by standard purification techniques, however it has been found that their removal is not essential for achieving the beneficial effects provided by the at least one compound of formula (I) (i.e., the presence of the impurities is not detrimental to the performance of the compounds of formula (I)) .
  • the collector compositions of the present invention may further comprise one or more collector compounds. It should be understood, however, that the compounds of formula (I) may be successfully used in flotation methods without necessarily requiring an additional collector compound. For the avoidance of any doubt, it should be understood that the optional collector compound is different to the bis-dithiocarbamate compounds of formula (I).
  • collector compositions disclosed herein comprise:
  • the optional collector compound(s) (ii) is not particularly limited.
  • flotation agents known as "collectors” are well-known to the skilled person and are generally used to facilitate the separation of a particular ore. Any such collector compounds are envisaged herein.
  • Preferred collector compound(s) (ii) are the surfactants, such as cationic surfactants, anionic surfactants, non-ionic surfactants, amphoteric surfactants, or a mixture of two or more of these. Below some examples of surfactants are given, but these should only be considered as suitable for the invention and are not to be regarded as limiting.
  • Suitable amphoteric surfactants include, but are not limited to, those of the formula [C]: wherein R 1 is a hydrocarbyl group with 8-22, preferably 12-18, carbon atoms; A is an alkyleneoxy group having 2-4, preferably 2, carbon atoms; p is a number 0 or 1; q is a number
  • R 2 is a hydrocarbyl group having 1-4 carbon atoms, preferably 1, or R 2 is the group wherein R 1 , A, p and q have the same meaning as above;
  • Y - is selected from the group consisting of COO - and SO 3 - , preferably COO - ;
  • n is a number 1 or 2, preferably 1;
  • M is a cation, which may be monovalent or divalent, and inorganic or organic, and r is a number 1 or 2.
  • the amphoteric surfactant of formula [C] may also be used in its acid form, where the nitrogen is protonated and no external cation is needed.
  • amphoteric surfactants have the formula [D]: wherein R 2 is a hydrocarbyl group with 8-22, preferably 12-18, carbon atoms, D is - CH 2 - or - CH 2 CH 2 -, k is 0-4, preferably 0-3, and most preferably 0-2, and M is hydrogen or a cation, such as sodium or potassium.
  • R 2 is a hydrocarbyl group with 8-22, preferably 12-18, carbon atoms
  • D is - CH 2 - or - CH 2 CH 2 -
  • k is 0-4, preferably 0-3, and most preferably 0-2
  • M is hydrogen or a cation, such as sodium or potassium.
  • the products where D is -CH 2 - are prepared by the reaction between a fatty amine and chloroacetic acid or its salts, and the products where D is -CH 2 CH 2 -are prepared by the reaction between a fatty amine and acrylic acid or esters thereof, in the latter case the reaction is followed by hydrolysis.
  • Suitable anionic surfactants include, but are not limited to, fatty acids (such as those with an C8 to C22 acyl group), alkylphosphates, such as those of formula [E], alkylsulfosuccinates, such as those of formula [F], alkylsarcosinates, such as those of formula [G], alkylmaleates, such as those of formula [H], alkylamidocarboxylates, such as those of formula [I], alkylglycinates, such as those of formula [J], alkyltaurates, such as those of formula [K], alkylhydroxamates, such as those of formula [L], wherein for each of formulae [E]-[L]:
  • Esters of the above alkylamidocarboxylates are also contemplated (preferably following the formula [I] of the alkylamidocarboxylates compounds, wherein Y is an alcohol derived hydrocarbon group, such as also described in US20160129456 ),
  • anionic surfactants include sulphonated fatty acids, alkylbenzensulphonates, such as those of formula [M], and alkylsulfonates, such as those of formula [N], wherein in formulae [M] and [N]:
  • Suitable nonionic surfactants include alcohols and alkoxylates (such as alkoxylated fatty alcohols RO(A) n H, alkoxylated fatty acids RC(O)O(A) n H), or alkyl glycosides (e.g., R(C 6 O 6 H 11 ) k ), or alkylethanolamides, such as those of the formulae [O] or [P], wherein R is linear or branched, saturated or unsaturated hydrocarbon group containing 1 to 24 carbon atoms; A is an alkylene oxide unit; n is from 0 to 50; Y is H, Na, K or an ammonium or alkylated ammonium; Z is -H, -CH 3 or -CH 2 CH 3; f is 1-25, preferably f is 1-15, and most preferable 1-10 and each f is independently 1 to 25; k is 1 or more, preferably about 1-5.
  • alcohols and alkoxylates such as alkoxylated
  • nonionic surfactants include alkyl nitrites, such as those of formulae [Q 1 ] and [Q 2 ], wherein, for each of formulae Q 1 and Q 2 , R is a linear or branched, substituted or unsubstituted, saturated or unsaturated, C10-C30 alkyl.
  • R is a linear or branched, substituted or unsubstituted, saturated or unsaturated, C10-C30 alkyl.
  • the compounds of formula [Q 2 ] may also be in dimeric form (such as when the R group is an unsaturated alkyl), one nonlimiting example of which is (7Z)-9,10-dinonyloctadec-7-enedinitrile ( CAS No. 68606-80-4 ).
  • Suitable cationic surfactants include, but are not limited to, fatty amines (preferably C8-C22, linear or branched alkyamines), fatty diamines (preferably C8-C22, linear or branched), alkyl etheramines (preferably C8-C22, linear or branched alky etheramines), alkyl etherdiamines (preferably C8-C22, linear or branched alkyl etherdiamines), alkyl esteramines (preferably C8-C22, linear or branched alkyl esteramines), quaternary ammonium surfactants, polyester polyamines (PEPA), and polyester polyquats (PEPQ).
  • fatty amines preferably C8-C22, linear or branched alkyamines
  • fatty diamines preferably C8-C22, linear or branched
  • alkyl etheramines preferably C8-C22, linear or branched alky etheramines
  • PEPA or PEPQ are related to polymeric components containing multiple amine or quaternary ammonium centres, respectively. Commonly, PEPA and PEPQ are obtained from reaction of an amine, dicarboxylic acid and hydrophobic precursor (for example, fatty acid or fatty alcohol).
  • Preferred PEPA and PEPQ cationic surfactants include, but are not limited to: wherein:
  • PEPQ cationic surfactants include: wherein:
  • the collector composition disclosed herein may comprise a mixture of two or more anionic and/or nonionic surfactants.
  • collector compound(s) (ii) include, but are not limited to, xanthates, such as those of formula [R], dithiophosphates, such as those of formulae [S 1 ] or [S 2 ], thionocarbamates, such as those of formula [T], dithiophosphinates, such as those of formulae [U 1 ] or [U 2 ],
  • the weight ratio of the one or more collector compounds (ii) to component (i) (the at least one bis-dithiocarbamate compound of formula (I) as defined above) in the collector composition is preferably from about 15:85 to 99:1, preferably about 20:80 to 98:2, preferably about 25:75 to 95:5.
  • the collector composition of the present disclosure comprises component (i) and optional component (ii) in a total amount of about 15 wt.% to about 100 wt.% (relative to the total weight of the collector composition), preferably in the above weight ratio (ii) to (i).
  • the collector compositions described above may further comprise a solvent.
  • Preferred solvents include, but are not limited to, water, alcohol(s), and mixtures thereof.
  • Preferred alcohols are the C1-C20 mono or polyhydric alcohols, such as, but not limited to, isopropyl alcohol, propylene glycol, polyethylene glycol, ethylene glycol, diethylene glycol, triethylene glycol, hydrocarbon oils, C6-C18 mono- and polyhydric alcohols, and mixtures thereof. If a solvent is used, then the collector composition preferably comprises at least 50 wt.%, more preferably at least 60 wt.%, and most preferably at least 65 wt.% of the solvent (relative to the total weight of the collector composition).
  • the present invention relates to a flotation method using the collector composition as described in detail above.
  • the collector composition is particularly suitable for treating sulfidic ores, such as copper-containing ores (e.g., chalcopyrite, chalcocite, bornite, malachite), zinc-containing ores (e.g., sphalerite), lead-containing ores (e.g., galena), nickel-containing ores (e.g.
  • pentlandite, millerite gold-containing ores (calaverite and electrum or gold is associated with pyrite, pyrrhotite, arsenopyrite, chalcopyrite, chalcocite, bornite, galena etc.), silver-containing ores (e.g., argentite or silver associated with pyrite, pyrrhotite, arsenopyrite, chalcopyrite, chalcocite, bornite, galena etc.), and iron/sulfur containing ores (e.g., pyrrhotite, pyrite, arsenopyrite).
  • gold-containing ores calaverite and electrum or gold is associated with pyrite, pyrrhotite, arsenopyrite, chalcopyrite, chalcocite, bornite, galena etc.
  • silver-containing ores e.g., argentite or silver associated with pyrite, pyrrhotite, ar
  • the collector composition disclosed herein is particularly suitable for:
  • the collector composition disclosed herein may be used in following flotation circuits and operations: Rougher, Scavenger, Cleaner flotation using mechanical, penumatic, froth separational or column flotation machines. Additionally and/or alternatively, the collector composition disclosed herein may be added directly to the milling stage of the ore before the actual conditioning or flotation stage.
  • the amount of collector composition added to the ore will in general be in the range of from about 5 to about 1000 g/ton dry ore, preferably in the range of from about 10 to about 500 g/ton dry ore, more preferably from about 15 to about 400 g/ton dry ore, more preferably from about 20 to about 200 g/ton dry ore. It should be understood that these values relate to the grams of actives content of the collector composition per ton of dry ore. For example, adding 100g of a 50% actives content collector composition (e.g., collector composition consisting of 50% actives and 50% solvent) to 1 ton of dry ore would result in a dosing of 50 g/ton collector composition.
  • a 50% actives content collector composition e.g., collector composition consisting of 50% actives and 50% solvent
  • reagents can be added either at the same time or, preferably, separately during the process and can include depressants, such as a polysaccharide, alkalized starch or dextrin, extender oils, frothers/froth regulators, such as pine oil, MIBC (methylisobutyl carbinol) and alcohols such as hexanol and alcohol ethoxylates/propoxylates, inorganic dispersants, such as silicate of sodium (water glass), calcium oxide and soda ash, and pH-regulators.
  • depressants such as a polysaccharide, alkalized starch or dextrin
  • extender oils frothers/froth regulators
  • frothers/froth regulators such as pine oil, MIBC (methylisobutyl carbinol) and alcohols such as hexanol and alcohol ethoxylates/propoxylates
  • inorganic dispersants such as silicate of sodium (water glass), calcium oxide and soda ash, and
  • the process to treat ores according to the present disclosure preferably comprises the steps of:
  • a 2 L round bottomed flask equipped with agitator, temperature controller/heating mantle, and condenser was charged with 435 g of water, 56 g of propylene glycol, and 183 g of 30 % NaOH.
  • 180 g of N-coco-1,3-diaminopropane pre-melted in a laboratory oven was added from a beaker to the reactor through a neck using a glass funnel, followed by 50 g of propylene glycol and 40 g of water to ensure a quantitative transfer from the beaker to the reactor.
  • 104 g of carbon disulfide was added to the reactor by slow-addition over 1.5 hr. at a temperature of 40 to 45 deg C using a reciprocating laboratory pump.
  • the reactor solution was then held at 40 to 45 deg C for a final reaction/cook period.
  • the reaction product was cooled, and the final pH was adjusted to a range of 12 to 13 using 50 % NaOH.
  • the product was a clear, orange/red, low viscosity liquid with 30 % actives content.
  • Example 1A The experiment described in Example 1A was repeated, but with propylene glycol replaced by isopropyl alcohol.
  • the product was a clear, orange/red, low viscosity liquid with 30 % actives content.
  • a 1 L round bottomed flask equipped with agitator, temperature controller/heating mantle, and condenser was charged with 247 g of water, 35 g of isopropyl alcohol, and 88 g of 30 % NaOH.
  • 110 g of N-tallow-1,3-diaminopropane (pre-melted in a laboratory oven) was added from a beaker to the reactor through a neck using a glass funnel, followed by 25 g of isopropyl alcohol and 30 g of water to ensure a quantitative transfer from the beaker to the reactor.
  • 51 g of carbon disulfide was added to the reactor by slow-addition over 1.5 hr. at a temperature of 40 to 45 deg C using a reciprocating laboratory pump.
  • the reactor solution was then held at 40 to 45 deg C for a final reaction/cook period.
  • the reaction product was cooled, and the final pH was adjusted to a range of 12 to 13 using 50 % NaOH.
  • the product was a clear, orange/red, low viscosity liquid with 30 % actives content.
  • collector Compound Example 3A Example 3B
  • Example 3C The following collector compounds were tested in the flotation of chalcopyrite/pyrite ore: Collector Compound Example 3A
  • Example 3B Example 3C
  • the following protocol was used in the flotation tests: 500 g of the ore was ground with 500 g of tap water in 6.4 kg stainless steel media during 4 min. This allowed to obtain the feed pulp with particle size distribution of p80 -150 ⁇ m. The pulp was transferred to the flotation cell of 1.4 L. The pulp was conditioned with 1% CaO solution at pH 10.5 during 2 min. The pulp was conditioned with 20 g/t of the collector (Example 1A) during 2 min. The pulp was conditioned with 20 g/t of 0.5% solution of MIBC frother during 10 sec before the actual flotation. Rougher flotation was performed during 5 min (the pH was controlled at 10.5 with CaO). The air flow was 3.5 L/min with 1000 rpm.
  • Example 3A Example 3B
  • Example 3C Performance Cu ore (Chalcopyrite / Pyrite) Cu grade, % 3.5 4.5 2.0 Cu recovery, % 92.4 92.4 80.9 S recovery, % 89.2 66.9 Not analyzed

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EP23164423.8A 2023-03-27 2023-03-27 Kollektorzusammensetzung Pending EP4438184A1 (de)

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EP23164423.8A EP4438184A1 (de) 2023-03-27 2023-03-27 Kollektorzusammensetzung

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA771182A (en) * 1967-11-07 B. Hudson George Dithiocarbamate ore collector agents
CA771181A (en) 1967-11-07 Du Pont Of Canada Limited Dithiocarbamate ore collector agents
EP0037861A1 (de) * 1980-03-24 1981-10-21 Tokyo Organic Chemical Industries, Ltd. Salze von Alkylenbisdithiocarbaminsäurederivaten, Verfahren zu ihrer Herstellung, sie enthaltende fungizide Zusammensetzungen und Verfahren zur Pilzbekämpfung
US4358368A (en) 1979-03-02 1982-11-09 Berol Kemi Ab Process for the froth flotation of calcium phosphate-containing minerals and flotation agents therefor
US4554068A (en) 1983-07-26 1985-11-19 Phillips Petroleum Company Ore flotation and flotation agents for use therein
US4702821A (en) 1985-02-26 1987-10-27 Phillips Petroleum Company Ore flotation and di-alkali metal-di(carboxyalkyl)dithiocarbamate and diammonium-di(carboxyalkyl)dithiocarbamate flotation agents for use therein
US4828687A (en) 1984-04-04 1989-05-09 Berol Kemi Ab Froth flotation process and collector therefor
US5013451A (en) * 1984-08-30 1991-05-07 Petrolite Corporation Methods for treating hydrocarbon recovery operations and industrial waters
US5112505A (en) * 1986-05-15 1992-05-12 Petrolite Corporation Certain dithiocarbamates and method of use for reducing asphaltene precipitation in asphaltenic reservoirs
US20080185317A1 (en) 2007-02-07 2008-08-07 Nagaraj Devarayasamudram R Novel dithiocarbamate collectors and their use in the beneficiation of mineral ore bodies
US20160129456A1 (en) 2013-07-05 2016-05-12 Akzo Nobel Chemicals International B.V. The Synthesis of New Anionic Surfactants and Their Use as Collectors in Froth Flotation of Non-Sulphidic Ores

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA771182A (en) * 1967-11-07 B. Hudson George Dithiocarbamate ore collector agents
CA771181A (en) 1967-11-07 Du Pont Of Canada Limited Dithiocarbamate ore collector agents
US4358368A (en) 1979-03-02 1982-11-09 Berol Kemi Ab Process for the froth flotation of calcium phosphate-containing minerals and flotation agents therefor
EP0037861A1 (de) * 1980-03-24 1981-10-21 Tokyo Organic Chemical Industries, Ltd. Salze von Alkylenbisdithiocarbaminsäurederivaten, Verfahren zu ihrer Herstellung, sie enthaltende fungizide Zusammensetzungen und Verfahren zur Pilzbekämpfung
US4554068A (en) 1983-07-26 1985-11-19 Phillips Petroleum Company Ore flotation and flotation agents for use therein
US4828687A (en) 1984-04-04 1989-05-09 Berol Kemi Ab Froth flotation process and collector therefor
US5013451A (en) * 1984-08-30 1991-05-07 Petrolite Corporation Methods for treating hydrocarbon recovery operations and industrial waters
US5013451B1 (de) * 1984-08-30 1992-12-08 Petrolite Corp
US4702821A (en) 1985-02-26 1987-10-27 Phillips Petroleum Company Ore flotation and di-alkali metal-di(carboxyalkyl)dithiocarbamate and diammonium-di(carboxyalkyl)dithiocarbamate flotation agents for use therein
US5112505A (en) * 1986-05-15 1992-05-12 Petrolite Corporation Certain dithiocarbamates and method of use for reducing asphaltene precipitation in asphaltenic reservoirs
US20080185317A1 (en) 2007-02-07 2008-08-07 Nagaraj Devarayasamudram R Novel dithiocarbamate collectors and their use in the beneficiation of mineral ore bodies
US20160129456A1 (en) 2013-07-05 2016-05-12 Akzo Nobel Chemicals International B.V. The Synthesis of New Anionic Surfactants and Their Use as Collectors in Froth Flotation of Non-Sulphidic Ores

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