US3768646A - Flotation of siliceous materials with diamine reaction products - Google Patents
Flotation of siliceous materials with diamine reaction products Download PDFInfo
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- US3768646A US3768646A US00181233A US3768646DA US3768646A US 3768646 A US3768646 A US 3768646A US 00181233 A US00181233 A US 00181233A US 3768646D A US3768646D A US 3768646DA US 3768646 A US3768646 A US 3768646A
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- acid
- amine
- flotation
- siliceous materials
- diamine
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- 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
- B03D2203/00—Specified materials treated by the flotation agents; specified applications
- B03D2203/02—Ores
- B03D2203/04—Non-sulfide ores
- B03D2203/06—Phosphate ores
Definitions
- N,N-diethylethylene diamine N,N-diethyl-N'- methylethylene diamine
- N,N-dimethyl-1,2-propane diamine N,N-diethyl-l,3-propane diamine
- N,N- dimethyl-l,3-propane-diamine N,N-dimethyethylene diamine and the like.
- N,N- dialkyl alkylene diamine or N,N-dia1kyl-N-alkyl alkylene diamine there may be present in the reaction system, reactive polyfunctional amines such as alkylene diamines, polyalkylene diamines, polyalkylene polyamines and the like.
- the amounts which may be present generally, range from about 0.6 to about 1.5 mol per mol of monofunctional diamine.
- saturated, unsaturated or hydroxylated fatty acids which may be reacted with an amine system containing N,N-dialkyl alkylene diamines and N,N-dialkyl- N'-alkyl alkylene diamines to provide the novel reagents of this invention may be varied widely. Preferably, however, they contain on the average, from about 8 to about 26 carbon atoms in the chain and may be derived from the fats or oils of either vegetable or animal origin.
- caprylic pelargonic, capric, undecanoic, lauric, tridecanoic, myristic, pentadecanoic, palmitic, margaric, stearic, nonadecanoic, arachidic, heneicosanoic, behenic, tricosanoic, lignoceric, pentacosanoic, cerotic, oleic, linoleic and the like.
- the acids may be synthetic or derived from natural vegetable or animal origins. Specific examples but no wise limiting of naturally occurring acids, which are usually mixtures of one or more of the above acids, there may be mentioned coconut oil acid,
- palm oil acid palm oil acid, cottonseed oil acid, corn oil acid, fish oil acid, peanut oil acid, soy bean oil acid, linseed oil acid, tall oil acid and the like.
- the amount of acid employed for the condensation reaction is an amount sufficient to provide from about 0.9 to about 3.7, preferably from about 1.0 to about 2.0 molar equivalent saturated, unsaturated fatty or hydroxylated fatty acid for each primary 7 or secondary amine available in the reaction system.
- Novel reagents provided in accordance with the practice of this invention are typically obtained by condensing the mixture of the fatty acid amines at a temperature from about to about 260 C for a period of time sufficient for the system to complete the reaction. Generally, depending on the mixture, condensation time from about 2 to about 6 hours or more will be required.
- condensation product obtained will vary somewhat depending upon the provided mol ratio of acid to amine. At lower mol ratios a condensation product will readily dissolve in water. At higher acid ratios, however, the product behaves generally more like the fatty acid used and shows a tendency to disperse rather than dissolve in solution.
- the tertiary amine groups are present in the amine condensation products of this invention and have been observed to provide the amine reaction products with selective activity for separating of ore values, such as phosphate rock, from siliceous materials by froth flotation.
- the tertiary amine groups also provide a functionality which allows the formation of salts by reaction with acids such as formic acid, acetic acid, propionic and hydrochloric acid, hydrofluoric acid and the like, to provide salts in which the novel fatty acid amines of this invention serve at a cation and where the anion is provided by the acid.
- acids such as formic acid, acetic acid, propionic and hydrochloric acid, hydrofluoric acid and the like, to provide salts in which the novel fatty acid amines of this invention serve at a cation and where the anion is provided by the acid.
- These salts are also active reagents for the beneficiation of ores and are particularly selective reagents for the flotation separation of ore values from siliceous materials.
- the activity of the amine reagents of this invention may be further promoted by the presence of certain acid like petroleum derivatives such as kerosene and the like in the system where flotation is carried out. They may also be used in conjunction with other beneficiating reagents for the separation of values from ores and the like.
- the amount of the amines of this invention employed in the beneficiation of ores is not narrowly critical.
- EXAMPLES 1 TO 15 EXAMPLE 18 The amine reagent prepared in Example 9 was used in place of amine prepared in Example 2. Florida phosphate rock was treated using amine in the concentra- A series of fatt acid-amine condensation reactions 5 I y tion of 0.45 lb. per ton of phosphate rock with kerosene carried out using a reactor equipped with a stirrer, a f th R It b r condenser and a temperature indicator. In each ini XS ene Separa are stance, the amine and acid were added in specified 8 own a e amounts to the reactor and the mixture heated with agi- TABLE v tation. An initial temperature increase was generally 10 lnsol.
- Example 16 The procedure of Example 16 was repeated except the amine was used at a concentration of 0.45 lb. per ton of ore process. The results are shown in Table 111:
- Example 20 21 The amine prepared in Example 2 was used for the beneficiation of phosphate at a high slurry density (22 23 percent) and compared to a commercial amine (Control A) which was a reaction product of a tall oil acid and diethylene triamine. As shown in Table VI, below, on a relative, comparative basis, phosphate loss in the tails was lower and insoluble retention by the float was also low.
- EXAMPLE 22 The performance of the amine of Example 2 was compared to the performance of an amine obtained by the condensation of tall oil acid with diethylene triamine at an acid to amine group ratio of approximately 1. The results are shown in Table VI] wherein the amount of siliceous insolubles in the concentrate was reduced by 50 percent:
- R RI! wherein R is hydrogen or an alkyl group, R, R" and R are independently alkyl groups and wherein each alkyl group contains from 1 to about 4 carbon atoms with from about 0.9 to about 3.7 mols per mol of primary and secondary amine groups of at least one fatty acid selected from the group consisting of saturated, unsaturated and hydroxylated fatty acids containing from about 8 to about 26 carbon atoms.
- the flotation reagent for the siliceous materials the salt obtained by reacting the condensation product obtained by reacting at least diamine having the structure:
- R is hydrogen or an alkyl group R, R" and R are independently alkyl groups and wherein each alkyl group contains from 1 to about 4 carbon atoms with from about 0.9 to about 3.7 mols per mol of primary and secondary amine groups of at least one fatty acid selected from the group consisting of saturated, unsaturated and hydroxylated fatty acids containing from about 8 to about 26 carbon atoms with an acid selected from the group consisting of formic acid, acetic acid, proprionic acid, hydrochloric acid and hydrofluoric and wherein the anion of the salt is provided by the acid.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the flotation separation of ore valves from siliceous materials by reagents obtained by the reaction of N,Ndialkyl alkylene diamines and N,N-dialkyl-N''-alkyl alkylene diamines with saturated, unsaturated and hydroxylated fatty acids.
Description
United States Patent [191 Grannen Oct. 30, 1973 FLOTATION OF SILICEOUS MATERIALS W1TH DIAMINE REACTION PRODUCTS Inventor: Edward A. Grannen, Upland,
Calif.
Assignce: Occidental Petroleum Corp.,
' Los Angeles. Calif.
Filed: Sept. 16, 1971 Appl. No.: 181,233
Related US. Application Data Division of Ser. No. 467, Jan. 2, 1970, abandoned.
US. Cl. 209/166, 260/4045 Int. Cl 803d l/02 Field of Search 209/166; 260/4045 References Cited UNITED STATES PATENTS 2,267,205 12/1941 Kyrides 209/166 2,329,149 9/1943 Weiner 209/166 2,494,132 1/1950 Jayne.... 209/166 2,569,417 9/1951 .layne.... 209/166 2,805,135 9/1957 Bell 260/4045 2,927,692 3/1960 Hollingsworth 209/167 Primary Examiner-Robert Halper AttorneyChristie, Parker & Hale 57 ABSTRACT 3 Claims, No Drawings DESCRIPTION RI! I wherein R is hydrogen or an alkyl group .and R'R" and R' are independently alkyl groups. The alkyl groups present may be straight chained or branched and preferably contain from about 1 to about 4 carbon atoms.
Illustrative but no wise limiting of the monofunctional N,N-dialkyl alkylene diamines and N,N-dialkyl- N'-alkylenediamines which may be used in accordance with the practice of this invention there may be mentioned N,N-diethylethylene diamine; N,N-diethyl-N'- methylethylene diamine; N,N-dimethyl-1,2-propane diamine; N,N-diethyl-l,3-propane diamine; N,N- dimethyl-l,3-propane-diamine; N,N-dimethyethylene diamine and the like.
In addition to at least one monofunctional N,N- dialkyl alkylene diamine or N,N-dia1kyl-N-alkyl alkylene diamine, there may be present in the reaction system, reactive polyfunctional amines such as alkylene diamines, polyalkylene diamines, polyalkylene polyamines and the like. The amounts which may be present, generally, range from about 0.6 to about 1.5 mol per mol of monofunctional diamine.
The saturated, unsaturated or hydroxylated fatty acids which may be reacted with an amine system containing N,N-dialkyl alkylene diamines and N,N-dialkyl- N'-alkyl alkylene diamines to provide the novel reagents of this invention may be varied widely. Preferably, however, they contain on the average, from about 8 to about 26 carbon atoms in the chain and may be derived from the fats or oils of either vegetable or animal origin. I v
Illustrative, but no wise limiting of the basic acid constituents which may be present in the fatty acids employed in accordance with the practice of this invention, there may be mentioned caprylic, pelargonic, capric, undecanoic, lauric, tridecanoic, myristic, pentadecanoic, palmitic, margaric, stearic, nonadecanoic, arachidic, heneicosanoic, behenic, tricosanoic, lignoceric, pentacosanoic, cerotic, oleic, linoleic and the like.
As indicated, the acids may be synthetic or derived from natural vegetable or animal origins. Specific examples but no wise limiting of naturally occurring acids, which are usually mixtures of one or more of the above acids, there may be mentioned coconut oil acid,
palm oil acid, cottonseed oil acid, corn oil acid, fish oil acid, peanut oil acid, soy bean oil acid, linseed oil acid, tall oil acid and the like.
As indicated, the amount of acid employed for the condensation reaction is an amount sufficient to provide from about 0.9 to about 3.7, preferably from about 1.0 to about 2.0 molar equivalent saturated, unsaturated fatty or hydroxylated fatty acid for each primary 7 or secondary amine available in the reaction system.
Accordingly, each of the N,N-dialkyl alkyl diamines and N,N-dialkyl-N'-alkyl alkylene diamines provided in Where polyfunctional amines, such as those set forth above, are present, a fatty acid equivalent, within the range prescribed above, should be provided for each amine group in the system having an active hydrogen, namely the primary and secondary amines.
Novel reagents provided in accordance with the practice of this invention are typically obtained by condensing the mixture of the fatty acid amines at a temperature from about to about 260 C for a period of time sufficient for the system to complete the reaction. Generally, depending on the mixture, condensation time from about 2 to about 6 hours or more will be required.
a The properties of the condensation product obtained will vary somewhat depending upon the provided mol ratio of acid to amine. At lower mol ratios a condensation product will readily dissolve in water. At higher acid ratios, however, the product behaves generally more like the fatty acid used and shows a tendency to disperse rather than dissolve in solution.
The tertiary amine groups are present in the amine condensation products of this invention and have been observed to provide the amine reaction products with selective activity for separating of ore values, such as phosphate rock, from siliceous materials by froth flotation.
The tertiary amine groups also provide a functionality which allows the formation of salts by reaction with acids such as formic acid, acetic acid, propionic and hydrochloric acid, hydrofluoric acid and the like, to provide salts in which the novel fatty acid amines of this invention serve at a cation and where the anion is provided by the acid. These salts are also active reagents for the beneficiation of ores and are particularly selective reagents for the flotation separation of ore values from siliceous materials.
Although they may be used alone in the beneficiation of mineral values, the activity of the amine reagents of this invention may be further promoted by the presence of certain acid like petroleum derivatives such as kerosene and the like in the system where flotation is carried out. They may also be used in conjunction with other beneficiating reagents for the separation of values from ores and the like.
The amount of the amines of this invention employed in the beneficiation of ores is not narrowly critical.
Generally, amounts from about 0.1 to about 2.0 or
EXAMPLES 1 TO 15 EXAMPLE 18 The amine reagent prepared in Example 9 was used in place of amine prepared in Example 2. Florida phosphate rock was treated using amine in the concentra- A series of fatt acid-amine condensation reactions 5 I y tion of 0.45 lb. per ton of phosphate rock with kerosene carried out using a reactor equipped with a stirrer, a f th R It b r condenser and a temperature indicator. In each ini XS ene Separa are stance, the amine and acid were added in specified 8 own a e amounts to the reactor and the mixture heated with agi- TABLE v tation. An initial temperature increase was generally 10 lnsol. observed when the amine and the fatty acid were wt BPL Assay mixed. With additional heating, water began to distill Assay Dism off at a temperature from between 140 and 150 C and Concentrate 84.7 73.9 97.6 3.7 continued to evolve until the temperature of the reac- Tails 53 mo 24 tion mass reached about 220 to 230 C. Reaction times Heads 100.0 64.1 100.0 varied from about 3 to about 6 hours. The nature of the EXAMPLE 19 amine fatty acids systems reacted and the mol ratios employed and general properties of the reaction mass The amine prepared in Example 1 was used to treat obtained are shown in Table l. a rougher phosphate rock containing about 10 percent TABLE I Mole ratio Wt. Wt. acid Example Fatty acid source percent Amine percent amine Remarks 1 Talloil 84 N,N-dimethyl-1,3-propane diamine..- 16 1.82 Opaque solution-two layers in standing 8 do 22 1. Clear brown solution. do 8.5 3.68 88 do 12 2.50 Soluble at do 13. 4 2. 25 Solids separation on standing.
d0 17. 2 1. 54 Opaque solution-no phase separation. .do 16 1.9 Clear, light yellow solution. 84 do. 16 1.83 Opaque solution. 77.8 .....do 12.2 1. 21. Insoluble. 91.4 o- 8.6 3.64 Opaque brown solution.
84 ..-.d 16 1.83 77 7 {N,N-diinethyl-1,3-propane diamine 11.1 1 21 Diethylene'triamine 11.2 5 {N,N-diinethyl-1,3-propane diamine 6.2 1 92 R*%idl%fl 2i 3'3 met y -propane iamine... {Diethyleiie triamine 6.2 92 5 n n heads 5 i i 'p p dlamil'le-n 1 92 Dlethylene triamine 1 Union Camp Corporation CX-l, reconstituted tall oil. 1 Arizona Chemical Company, Acintol H-2122 14. 1%? 9 1 11 1 99. 9p ease 2291 EXAMPLE 16 The amine reagent prepared in Example 2 was used as a beneficiation reagent for the cleaner float of a Florida phosphate rock containing 10 percent insolubles in a concentration of 0.3 lb. per ton of phosphate rock. Kerosene was present as a frother. The results of the froth flotation separation are shown in Table 11:
The procedure of Example 16 was repeated except the amine was used at a concentration of 0.45 lb. per ton of ore process. The results are shown in Table 111:
TABLE lll lniiol. BPL Ansiiyflu Wt. Assay ('70 P 0 'Diinr.(%) Concentrutc 84.1 73.7 97.3 4.0 Tails 15.9 9.0 2.3 Heads 100.0 63.1 99.6
insolubles in a concentration of 0.5 lb. per ton. The results are shown in Table V:
TABLE V BPL, Wt.% lnsol. Wt.% Yield, BPL Concentrate 69.2 2.6 98% Tails 93.96
I EXAMPLE 20 21 The amine prepared in Example 2 was used for the beneficiation of phosphate at a high slurry density (22 23 percent) and compared to a commercial amine (Control A) which was a reaction product of a tall oil acid and diethylene triamine. As shown in Table VI, below, on a relative, comparative basis, phosphate loss in the tails was lower and insoluble retention by the float was also low.
EXAMPLE 22 The performance of the amine of Example 2 was compared to the performance of an amine obtained by the condensation of tall oil acid with diethylene triamine at an acid to amine group ratio of approximately 1. The results are shown in Table VI] wherein the amount of siliceous insolubles in the concentrate was reduced by 50 percent:
What is claimed is:
1. In a process for the flotation of siliceous materials from mineral values, the use as the flotation reagent for the siliceous materials, the condensation product obtained by reacting at least diamine having the structure:
R RI! wherein R is hydrogen or an alkyl group, R, R" and R are independently alkyl groups and wherein each alkyl group contains from 1 to about 4 carbon atoms with from about 0.9 to about 3.7 mols per mol of primary and secondary amine groups of at least one fatty acid selected from the group consisting of saturated, unsaturated and hydroxylated fatty acids containing from about 8 to about 26 carbon atoms.
2. A process as claimed in claim 1 in which the fatty acid in the reaction product is present in the amount of from about 1.0 to about 1.5 mols per mol or primary and secondary amine groups present in the reactive amine system.
3. In a process for the flotation of siliceous materials from mineral values, the use as the flotation reagent for the siliceous materials, the salt obtained by reacting the condensation product obtained by reacting at least diamine having the structure:
wherein R is hydrogen or an alkyl group R, R" and R are independently alkyl groups and wherein each alkyl group contains from 1 to about 4 carbon atoms with from about 0.9 to about 3.7 mols per mol of primary and secondary amine groups of at least one fatty acid selected from the group consisting of saturated, unsaturated and hydroxylated fatty acids containing from about 8 to about 26 carbon atoms with an acid selected from the group consisting of formic acid, acetic acid, proprionic acid, hydrochloric acid and hydrofluoric and wherein the anion of the salt is provided by the acid.
Claims (2)
- 2. A process as claimed in claim 1 in which the fatty acid in the reaction product is present in the amount of from about 1.0 to about 1.5 mols per mol or primary and secondary amine groups present in the reactive amine system.
- 3. In a process for the flotation of siliceous materials from mineral values, the use as the flotation reagent for the siliceous materials, the salt obtained by reacting the condensation product obtained by reacting at least one diamine having the structure:
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US18123371A | 1971-09-16 | 1971-09-16 |
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US3768646A true US3768646A (en) | 1973-10-30 |
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US00181233A Expired - Lifetime US3768646A (en) | 1971-09-16 | 1971-09-16 | Flotation of siliceous materials with diamine reaction products |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4054516A (en) * | 1974-03-04 | 1977-10-18 | Director-General Of The Agency Of Industrial Science And Technology | Method for selectively capturing metal ions |
US4147614A (en) * | 1976-06-10 | 1979-04-03 | Theodor Gambopoulos | Aqueous mixture of diesel oil, pine oil and diamine for conditioning of crushed magnesite ore in magnetic beneficiation process |
US4460460A (en) * | 1982-04-13 | 1984-07-17 | Mobil Oil Corporation | Beneficiation of ores |
US20130119702A1 (en) * | 2010-04-09 | 2013-05-16 | Dimitrios A. Hatzikakidis | Pair of symmetrical, revolving, dihedral, semi-permeable aerodynamic devices |
WO2021123904A1 (en) | 2019-12-17 | 2021-06-24 | Momentive Performance Materials Gmbh | Polymeric fatty acid compounds for the treatment of fibrous amino acid-based substrates, especially hair |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2267205A (en) * | 1938-08-04 | 1941-12-23 | Monsanto Chemicals | Detergent |
US2329149A (en) * | 1940-11-04 | 1943-09-07 | Bonneville Ltd | Flotation process |
US2494132A (en) * | 1948-03-10 | 1950-01-10 | American Cyanamid Co | Beneficiation of acidic minerals |
US2569417A (en) * | 1948-03-10 | 1951-09-25 | American Cyanamid Co | Beneficiation of acidic minerals |
US2805135A (en) * | 1954-08-25 | 1957-09-03 | Eastman Kodak Co | Stabilized hydrocarbon fuel oil compositions and stabilizaers therefor |
US2927692A (en) * | 1955-12-12 | 1960-03-08 | Smith Douglass Company Inc | Concentration of minerals |
-
1971
- 1971-09-16 US US00181233A patent/US3768646A/en not_active Expired - Lifetime
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2267205A (en) * | 1938-08-04 | 1941-12-23 | Monsanto Chemicals | Detergent |
US2329149A (en) * | 1940-11-04 | 1943-09-07 | Bonneville Ltd | Flotation process |
US2494132A (en) * | 1948-03-10 | 1950-01-10 | American Cyanamid Co | Beneficiation of acidic minerals |
US2569417A (en) * | 1948-03-10 | 1951-09-25 | American Cyanamid Co | Beneficiation of acidic minerals |
US2805135A (en) * | 1954-08-25 | 1957-09-03 | Eastman Kodak Co | Stabilized hydrocarbon fuel oil compositions and stabilizaers therefor |
US2927692A (en) * | 1955-12-12 | 1960-03-08 | Smith Douglass Company Inc | Concentration of minerals |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4054516A (en) * | 1974-03-04 | 1977-10-18 | Director-General Of The Agency Of Industrial Science And Technology | Method for selectively capturing metal ions |
US4147614A (en) * | 1976-06-10 | 1979-04-03 | Theodor Gambopoulos | Aqueous mixture of diesel oil, pine oil and diamine for conditioning of crushed magnesite ore in magnetic beneficiation process |
US4460460A (en) * | 1982-04-13 | 1984-07-17 | Mobil Oil Corporation | Beneficiation of ores |
US20130119702A1 (en) * | 2010-04-09 | 2013-05-16 | Dimitrios A. Hatzikakidis | Pair of symmetrical, revolving, dihedral, semi-permeable aerodynamic devices |
US8870264B2 (en) * | 2010-04-09 | 2014-10-28 | Dimitrios A. Hatzikakidis | Pair of symmetrical, revolving, dihedral, semi-permeable aerodynamic devices |
US20150232136A1 (en) * | 2010-04-09 | 2015-08-20 | Dimitrios A. Hatzikakidis | Repair and/or reconpair of symmetrical, revolving, dihedral, semi-permeable aerodynamic devices |
US9415815B2 (en) * | 2010-04-09 | 2016-08-16 | Dimitrios A. Hatzikakidis | Repair and/or reconpair of symmetrical, revolving, dihedral, semi-permeable aerodynamic devices |
WO2021123904A1 (en) | 2019-12-17 | 2021-06-24 | Momentive Performance Materials Gmbh | Polymeric fatty acid compounds for the treatment of fibrous amino acid-based substrates, especially hair |
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