IP Library Granted Patent US 10,100,146
Granted Patent B2
US 10,100,146 · App. 15/101,300 · Granted Oct 16, 2018

Polyester polyquaternary ammonium compound collectors for reverse froth flotation of silicates from nonsulfidic ores

Inventors: Natalija Smolko-Schvarzmayr (Hjälteby, SE); Anders Klingberg (Henån, SE)
Assignee: AKZO NOBEL CHEMICALS INTERNATIONAL, B.V.
C08G63/916B03D1/011B03D1/016B03D1/02B03D1/021C07C229/24C07C229/26C07D219/06B03D2201/02B03D2201/06B03D2203/06
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Quick Facts
Patent No.
US 10,100,146
App. No.
15/101,300
Granted
Oct 16, 2018
Kind
B2
Abstract

The present invention relates to a compound obtainable by the condensation of a polyol having 3-4 hydroxyl groups, adicarboxylic acid or a derivative thereof, an alkanolamine and a fatty acid, followed by reaction with an alkylating agent. This compound is useful as a collector in a process for the reverse froth flotation of non-sulfidic ores containing silicate as impurities, especially phosphate ores.

Claims (52)

1. A compound produced by condensation of at least one polyol having 3-4 hydroxyl groups or an alkoxylated product thereof having the formula

where Z=—(CH 2 CH(CH 3 )O) m1 (CH 2 CH 2 O) o (CH 2 CH(CH 3 )O) m2 T, where T is H, m1 and m2 is independently a number 0-4, and o is 0 or a number from 1 to 10; Y=—CH 2 OZ, —CH 2 CH 3 or —OZ;

X=H or CH 2 OZ;

and V=Z or

at least one dicarboxylic acid or a derivative thereof having the formula (IIa) or (IIb)

where D is —OH, —Cl, or —OR 4 , where R 4 is a C1-C4 alkyl group; R3 is a bond, an alkylene radical of formula —(CH 2 ) z —, in which z is an integer from 1 to 10, and in which the alkylene radical may be substituted by 1 or 2 —OH groups; the group —CH═CH—, a cycloalkylene, a cycloalkenylene, or an arylene group;

at least one alkanolamine having the formula (III)

wherein each x independently is a number between 1 and 5, and the sum of all x on average is a number between 2 and 10, AO is an alkyleneoxy group having 2-4 carbon atoms, R 5 is a C1-C4 alkyl group, or [AO] x H; and

at least one fatty acid having the formula (IV)

R(C═O)OH  (IV)

where R is a hydrocarbyl group having from 7 to 23, carbon atoms, optionally substituted;

followed by reaction with an alkylating agent, suitably a C1-C4 alkyl halide, or dimethyl sulphate, wherein the compound is produced by a process that includes the steps of

1) reacting a mixture comprising the at least one alkanolamine, the at least one fatty acid, the at least one dicarboxylic acid and the at least one polyol having 3-4 hydroxyl groups in the absence of C2-C22 alcohols to form a polyester, and

2) quaternizing the resulting polyester by with the alkylating agent.

2. A compound according to claim 1 , where Y is —O(CH 2 CH(CH 3 )O) m1 (CH 2 CH 2 O) o (CH 2 CH(CH 3 )O) m2 T, X is H, T is H, and V and Z are both —(CH 2 CH(CH 3 )O) m1 (CH 2 CH 2 O) o (CH 2 CH(CH 3 )O) m2 T.

3. A compound according to claim 1 where R 5 is a methyl group, A is —CH 2 CH 2 — and the sum of all x is 2.

4. A compound according to claim 1 , where the alkylating agent is a C1-C4 alkyl halide.

5. A compound according to claim 1 having the structural formula

where R is a hydrocarbyl group having from 7 to 23, carbon atoms, optionally substituted; and

R′ is H or R(C═O); n is an integer 0-10; m is a number 1-3 and k is a number 2-7.

6. A method for reverse froth flotation for ores containing phosphate or ferruginous minerals containing silicate as impurities, in which method a compound is used as a collector, the compound being produced by condensation of at least one polyol having 3-4 hydroxyl groups or an alkoxylated product thereof having the formula

where Z=—(CH 2 CH(CH 3 )O) m1 (CH 2 CH 2 O) o (CH 2 CH(CH 3 )O) m2 T, where T is H, m1 and m2 is independently a number 0-4, and o is 0 or a number from 1 to 10; Y=—CH 2 OZ, —CH 2 CH 3 or —OZ;

X=H or CH 2 OZ;

and V=Z or

at least one dicarboxylic acid or a derivative thereof having the formula (IIa) or (IIb)

where D is —OH, —Cl, or —OR 4 , where R 4 is a C1-C4 alkyl group; R3 is a bond, an alkylene radical of formula —(CH 2 ) z —, in which z is an integer from 1 to 10, and in which the alkylene radical may be substituted by 1 or 2 —OH groups; the group —CH═CH—, a cycloalkylene, a cycloalkenylene, or an arylene group;

at least one alkanolamine having the formula (III)

wherein each x independently is a number between 1 and 5, and the sum of all x on average is a number between 2 and 10, AO is an alkyleneoxy group having 2-4 carbon atoms, R 5 is a C1-C4 alkyl group, or [AO] x H; and

at least one fatty acid having the formula (IV)

R(C═O)OH  (IV)

where R is a hydrocarbyl group having from 7 to 23, carbon atoms, optionally substituted;

followed by reaction with an alkylating agent, suitably a C1-C4 alkyl halide, or dimethyl sulphate wherein the compound is produced by a process that includes the steps of

1) reacting a mixture comprising the at least one alkanolamine, the at least one fatty acid, the at least one dicarboxylic acid and the at least one polyol having 3-4 hydroxyl groups to form a polyester, and

2) quaternizinq the resulting polyester by with the alkylating agent.

7. A method according to claim 6 wherein the ore is a phosphate ore.

8. A method according to claim 7 which comprises the steps of

a) conditioning a pulped phosphate ore, wherein the phosphate ore comprises an apatite mineral or a mixture of such minerals, and gangue minerals, with an effective amount of a silicates collector reagent, which is a compound as defined in claim 1 , and optionally other flotation aids and

b) performing a reverse froth flotation process to remove the silicates from the apatite mineral.

9. A pulp comprising a crushed and ground phosphate ore, a compound, and optionally a depressant, wherein the compound is produced by condensation of at least one polyol having 3-4 hydroxyl groups or an alkoxylated product thereof having the formula

where Z=—(CH 2 CH(CH 3 )O) m1 (CH 2 CH 2 O) o (CH 2 CH(CH 3 )O) m2 T, where T is H, m1 and m2 is independently a number 0-4, and o is 0 or a number from 1 to 10; Y=—CH 2 OZ, —CH 2 CH 3 or —OZ;

X=H or CH 2 OZ;

and V=Z or

at least one dicarboxylic acid or a derivative thereof having the formula (IIa) or (IIb)

where D is —OH, —Cl, or —OR 4 , where R 4 is a C1-C4 alkyl group; R3 is a bond, an alkylene radical of formula —(CH 2 ) z —, in which z is an integer from 1 to 10, and in which the alkylene radical may be substituted by 1 or 2 —OH groups; the group —CH═CH—, a cycloalkylene, a cycloalkenylene, or an arylene group;

at least one alkanolamine having the formula (III)

wherein each x independently is a number between 1 and 5, and the sum of all x on average is a number between 2 and 10, AO is an alkyleneoxy group having 2-4 carbon atoms, R 5 is a C1-C4 alkyl group, or [AO] x H; and

at least one fatty acid having the formula (IV)

R(C═O)OH  (IV)

where R is a hydrocarbyl group having from 7 to 23, carbon atoms, optionally substituted;

followed by reaction with an alkylating agent, suitably a C1-C4 alkyl halide, or dimethyl sulphate wherein the compound is produced by a process that includes the steps of

1) reacting a mixture comprising the at least one alkanolamine, the at least one fatty acid, the at least one dicarboxylic acid and the at least one polyol having 3-4 hydroxyl groups to form a polyester, and

2) quaternizing the resulting polyester by with the alkylating agent.

Assignments (3)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2016
From: SMOLKO-SCHVARZMAYR, NATALIJA; KLINGBERG, ANDERS
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 038788/0794 →
Priority Claims (2)
EP 13198074 · Dec 18, 2013 · regional
EP 13198086 · Dec 18, 2013 · regional
Continuity (1)
Related Publication 20160304663A1 · Oct 20, 2016