Quaternary dialkanolamine esters
View Patent ↗The invention relates to novel quaternary ammonium compounds of the esterquat type, to a method for the production thereof, and to the use thereof in formulations.
1. A mixture of quaternary dialkanolamine esters of general formula (I)
where
Y 1 and Y 2 are the same or different and are each independently an alkyl radical having 1 to 6 carbon atoms, a benzyl radical or H,
n=1 to 4,
A- is an anion,
X 1 and X 2 are the same or different and are each independently selected from groups (a), (b), (c) and (d), said groups consisting of
(a) acyl radicals containing 6 to 14 carbon atoms,
(b) acyl radicals containing 15 to 20 carbon atoms and at least one carbon-carbon double bond,
(c) acyl radicals containing 20 to 24 carbon atoms, and
(d) acyl radicals which contain 3 to 28 carbon atoms and are not included in groups (a) to (c), or H,
with the proviso that each molecule of general formula (I) contains a numerical average of
0.30 to 1.50 radicals from group (a),
0.10 to 1.30 radicals from group (b),
0.40 to 1.60 radicals from group (c),
0 to 0.20 radical from group (d),
and the numerical averages per molecule of the radicals from groups (a), (b), (c) and (d) add up to 2.
2. The mixture of quaternary dialkanolamine esters as claimed in claim 1 , wherein
acyl radicals from group (a) are selected from C 5 H 11 CO—, C 7 H 15 CO—, C 9 H 19 CO—, C 11 H 23 CO— and C 13 H 27 CO—,
acyl radicals from group (b) are selected from C 15 H 29 CO—, C 17 H 33 CO—, C 17 H 31 CO—, C 17 H 29 CO—, C 19 H 37 CO—, C 19 H 31 CO— and C 19 H 29 CO—,
acyl radicals from group (c) are selected from C 19 H 39 CO—, C 21 H 43 CO— and C 23 H 47 CO—, and
acyl radicals from group (d) are selected from acyl radicals of the carboxylic acids which are additionally present in technical grade mixtures of the carboxylic acids which determine the acyl radical from groups (a), (b) and (c).
3. The mixture of quaternary dialkanolamine esters as claimed in claim 1 , wherein
acyl radicals from group (a) are selected from C 11 H 23 CO—,
acyl radicals from group (b) are selected from C 15 H 29 CO—, C 17 H 33 CO, C 17 H 31 CO—, C 17 H 29 CO— and C 19 H 37 CO— in a weight ratio of 3-7:68-76:5-13:1-3:0-2,
acyl radicals from group (c) are selected from C 19 H 39 CO—, C 21 H 43 CO—, C 23 H 47 CO— in a weight ratio of 4-8:85-99:0-3.
4. The mixture of quaternary dialkanolamine esters as claimed in claim 1 , wherein the acyl radicals from groups (a) to (d) are determined via the acyl radicals of a mixture consisting of
technical grade lauric acid,
technical grade oleic acid, and
technical grade behenic acid.
5. The mixture of quaternary dialkanolamine esters as claimed in claim 1 , wherein the numerical average of the molar ratio of the sum of acyl radicals from group (a) and group (b) to acyl radicals from group (c) is 1:0.67 to 4.
6. A process for preparing a mixture of quaternary dialkanolamine esters in accordance with claim 1 , comprising the process steps of
A) reacting an alkyldialkanolamine in which the two alkanol groups are selected from the group consisting of —CH 2 OH, —C 2 H 4 OH, —C 3 H 6 OH and —C 4 H 8 OH and the alkyl group is selected from the group consisting of alkyl radicals having 1-6 carbon atoms with a mixture of carboxylic acids consisting of
(e) carboxylic acid containing 6 to 14 carbon atoms,
(f) carboxylic acid containing 15 to 20 carbon atoms and at least one carbon-carbon double bond, and
(g) carboxylic acid containing 20 to 24 carbon atoms, and optionally
(h) carboxylic acid which contains 3 to 28 carbon atoms and is not included in groups (e), (f) and (g),
B) reacting the product from process step A) with a quaternizing agent selected from dialkyl sulfates, alkyl halides and benzyl halides, and/or
C) neutralizing the reaction mixture with an acid,
with the proviso that, based on all carboxylic acids from groups (e), (f), (g) and (h), 0 to 10 mol % of carboxylic acids from group (h) is used.
7. The process as claimed in claim 6 , wherein, for each mole of alkyldialkanolamine used in process step (A),
0.30 to 1.50 mol of carboxylic acid from group (e),
0.10 to 1.30 mol of carboxylic acid from group (f), and
0.40 to 1.60 mol of carboxylic acid from group (g)
are used.
8. The process as claimed in claim 6 , wherein, for each mole of alkyldialkanolamine, carboxylic acids from groups (e), (f), (g) and optionally (h) are used in a total amount of 1.80 to 2.5 mol.
9. The process as claimed in claim 6 , wherein, in process step B), at least one solvent selected from the group consisting of short-chain alcohols, fatty alcohols, polyols and carbonates is used.
10. A composition comprising:
a mixture of quaternary dialkanolamine esters of general formula (I)
where
Y 1 and Y 2 are the same or different and are each independently an alkyl radical having 1 to 6 carbon atoms, a benzyl radical or H,
n=1 to 4,
A- is an anion,
X 1 and X 2 are the same or different and are each independently selected from groups (a), (b), (c) and (d), said groups consisting of
(a) acyl radicals containing 6 to 14 carbon atoms,
(b) acyl radicals containing 15 to 20 carbon atoms and at least one carbon-carbon double bond,
(c) acyl radicals containing 20 to 24 carbon atoms, and
(d) acyl radicals which contain 3 to 28 carbon atoms and are not included in groups (a) to (c), or H,
with the proviso that each molecule of the general formula (I) contains a numerical average of
0.30 to 1.50 radicals from group (a),
0.10 to 1.30 radicals from group (b),
0.40 to 1.60 radicals from group (c),
0 to 0.20 radical from group (d),
and the numerical averages per molecule of the radicals from groups (a), (b), (c) and (d) add up to 2, and at least one solvent.
11. The composition as claimed in claim 10 , wherein the solvent is isopropanol or propylene carbonate.
12. A formulation comprising a mixture of quaternary dialkanolamine esters of general formula (I)
where
Y 1 and Y 2 are the same or different and are each independently an alkyl radical having 1 to 6 carbon atoms, a benzyl radical or H,
n=1 to 4,
A- is an anion,
X 1 and X 2 are the same or different and are each independently selected from groups (a), (b), (c) and (d), said groups consisting of
(a) acyl radicals containing 6 to 14 carbon atoms,
(b) acyl radicals containing 15 to 20 carbon atoms and at least one carbon-carbon double bond,
(c) acyl radicals containing 20 to 24 carbon atoms, and
(d) acyl radicals which contain 3 to 28 carbon atoms and are not included in groups (a) to (c), or H,
with the proviso that each molecule of general formula (I) contains a numerical average of
0.30 to 1.50 radicals from group (a),
0.10 to 1.30 radicals from group (b),
0.40 to 1.60 radicals from group (c),
0 to 0.20 radical from group (d),
and the numerical averages per molecule of the radicals from groups (a), (b), (c) and (d) add up to 2, and at least one solvent.
13. The quaternary dialkanolamine ester as claimed in claim 1 , wherein said anion is selected from the group consisting of chloride, bromide, methyl sulfate, tosylate, phosphate, sulfate, hydrogen sulfate, lactate, acetate and citrate.
14. The formulation of claim 12 , wherein the quaternary dialkanoline esters and/or said composition is present in an amount of 0.5 to 4% by weight, based on the overall formulation.
15. The formulation of claim 12 , wherein the quaternary dialkanoline esters and/or said composition is present in an amount of 1-3% by weight, based on the overall formulation.
16. The formulation of claim 12 , wherein said formulation is an aqueous formulation.
17. The formulation of claim 12 , wherein said formulation has a pH of 3.5 to 5.
18. The formulation of claim 12 , wherein said formulation is a cosmetic or pharmaceutical formulation and care and cleaning formulation for use in the domestic and industrial sector.
19. The formulation of claim 18 , wherein said care and cleaning composition is a skin care composition, haircare composition and/or a fabric softener.