Long-chain alkyl esterquats for highly viscous laundry and cleaning formulations

Abstract

The invention relates to specific active compositions for producing highly viscous laundry and cleaning formulations, particularly laundry fabric softeners, to a method for the production thereof and to said laundry and cleaning formulations. High viscosity can be achieved in the products according to the invention despite a low concentration of active compositions and without using additional thickeners.

Claims

1. An active composition for producing laundry and cleaning formulations, comprising a mixture of two or more quaternary ammonium salts of the general formula I): ##STR00004## wherein: R.sup.1 is a linear or branched hydrocarbon radical having an iodine number of from 0 to 5, and comprising 14 to 20 carbon atoms; R.sup.2, R.sup.4 are the same or different, each independently selected from divalent, linear hydrocarbon radicals comprising 1 to 4 carbon atoms; R.sup.3 is hydrogen or an acyl radical of a fatty acid comprising a chain length of 12 to 22 carbon atoms; R.sup.5 is the same as, or different from, R.sup.3, and is an acyl radical of a fatty acid comprising a chain length of 12 to 22 carbon atoms; R.sup.6 is methyl or ethyl; X.sup.− is methylsulfate or ethylsulfate; wherein: the amount ratio of the quaternary ammonium salts of the general formula I) in the mixture is a result of one or more amine(s) of the general formula II): ##STR00005## wherein: R.sup.1, R.sup.2 and R.sup.4 have the same definition as in formula I), being reacted with one or more fatty acids corresponding to R.sup.3 and R.sup.5, in the molar ratio of the sum of all amines of the general formula II) to the sum of all fatty acids of from 0.8 to 1.5.

2. The active composition of claim 1, wherein: the amount ratio of the quaternary ammonium salts of the general formula I) in the mixture is a result of one or more amine(s) of the general formula II) where R.sup.1, R.sup.2 and R.sup.4 have the same definition as in formula I), being reacted with one or more fatty acids corresponding to R.sup.3 and R.sup.5, in the molar ratio of the sum of all amines of the general formula II) to the sum of all fatty acids of from 0.9 to 1.2.

3. The active composition of claim 1, wherein the active composition is for producing a fabric softener formulation, wherein: R.sup.1 is a linear or branched hydrocarbon radical having an iodine number of from 0 to 5, and comprising 16 to 18 carbon atoms; R.sup.2, R.sup.4 are ethylene; R.sup.3 is hydrogen or an acyl radical of a fatty acid having a chain length of 16 to 18 carbon atoms; R.sup.5 is the same as or different from R.sup.3, and is an acyl radical of a fatty acid having a chain length of 16 to 18 carbon atoms; R.sup.6 is methyl.

4. The active composition of claim 1, wherein one or both R.sup.2 and R.sup.4 radicals are ethylene.

5. The active composition of claim 1, wherein R.sup.3 and R.sup.5 are radicals of the same fatty acid or fatty acid mixture.

6. The active composition of claim 1, wherein the mixture comprises quaternary ammonium compounds of the general formula I), wherein: R.sup.3, R.sup.5 are the same or different, each independently being an acyl radical of a fatty acid having a chain length of 16 to 18 carbon atoms; R.sup.6 is methyl.

7. The active composition of claim 1, wherein: R.sup.3 and R.sup.5 are acyl radicals selected from: plant or tallow fatty acids, having an iodine number from 0 to 50; plant or tallow fatty acids having an iodine number of less than or equal to 10.

8. The active composition of claim 1, wherein: R.sup.3 and R.sup.5 are acyl radicals selected from: plant or tallow fatty acids, having an iodine number from 10 to 25; plant or tallow fatty acids having an iodine number of from 0 to 5.

9. A method for preparing the active composition of claim 1, comprising: a) reacting one or more amine(s) of the general formula II), ##STR00006## wherein R.sup.1, R.sup.2 and R.sup.4 have the same definition as in claim 1, with one or more fatty acid(s) having a chain length of 12 to 22 carbon atoms, and the molar ratio of the sum of all amines of the general formula II) to the sum of all fatty acids of from 0.8 to 1.5; b) reacting the amines of step a) with an alkylating agent, selected from the group consisting of: dimethyl sulfate and diethyl sulfate, for preparing quaternary ammonium salts of the formula I).

10. The method of claim 9, further comprising: c) diluting the active composition mixture obtained according to step b) with 30-40% by weight, of a water-miscible solvent.

11. The method of claim 9, and further comprising: c) diluting the active composition mixture obtained according to step b) with 10-20% by weight, of a water-miscible solvent.

12. The method of claim 9, and further comprising: c) diluting the active composition mixture obtained according to step b) with one or more solvents selected from the group consisting of: ethanol; 1-propanol; 2-propanol; 1,2-ethylene glycol; 1,2-propylene glycol; 1,3-propylene glycol; dipropylene glycol; dipropylene glycol; ethylene glycol ether; and propylene glycol ether.

13. The method of claim 9, wherein R.sup.1, R.sup.2 and R.sup.4 have the same definition as in claim 1, with one or more fatty acid(s) having a chain length of 16 to 18 carbon atoms, and wherein the molar ratio of the sum of all amines of the general formula II to the sum of all fatty acids of from 0.9 to 1.2.

14. A laundry and cleaning formulation, comprising an active composition according to claim 1.

15. The laundry and cleaning formulation of claim 14, wherein the formulation is a fabric softener formulation.

16. The laundry and cleaning formulation of claim 14, comprising the active composition in from 1% by weight to 6% by weight, where the percentages by weight refer to the total composition.

17. The laundry and cleaning formulation of claim 14, comprising the active composition in from 2% by weight to 5% by weight, where the percentages by weight refer to the total composition.

18. The laundry and cleaning formulation of claim 14, comprising a viscosity of more than 500 mPas, measured using a Brookfield LVT viscometer and a spindle suitable for the viscosity range at a temperature of 25° C. and 30 rev/min.

19. The laundry and cleaning formulation of claim 14, comprising a viscosity of more than 1000 mPas, measured using a Brookfield LVT viscometer and a spindle suitable for the viscosity range at a temperature of 25° C. and 30 rev/min.

Description

6. EXAMPLES

(1) The examples adduced hereinafter describe the present invention by way of example, without any intention that the invention, the scope of application of which is apparent from the entirety of the description and the claims, should be restricted to the embodiments specified in the examples.

(2) 6.1 Starting Materials Used:

(3) 6.1.1 Amines of the General Formula II:

(4) TABLE-US-00001 TABLE 1 R.sup.1 Trade Amine (all % figures are mol %) R.sup.2 R.sup.3 name Source A1 Stearyl having 93% C18, C.sub.2H.sub.4 C.sub.2H.sub.4 Varonic Evonik 5% C16, 2% > C20 S 202 Corporation, with IN = 0-3.0 USA A2 Tallow having 3% C14, C.sub.2H.sub.4 C.sub.2H.sub.4 Varonic Evonik 30% C16, 67% C18 T 202 Corporation, with IN = 38.0-54.0 USA A3 Hydr. tallow C.sub.2H.sub.4 C.sub.2H.sub.4 Varonic Evonik having 3% C14, U 202 Corporation, 30% C16, 67% C18 USA with IN <= 3.0
6.1.2 Fatty Acids:

(5) TABLE-US-00002 TABLE 2 Fatty acids Source IN FA1 Tallow fatty acid, Edenor T20, KLK Oleo 18-22 FA2 Tallow fatty acid, Raciacid 0474, Oleon 30-42 FA3 Hydrogenated tallow fatty acid, Baerocid SMS-1A, <1.0 Baerlocher FA4 Stearic fatty acid, plant-based, Pristeren 4928, Croda <2.0
6.1.3 Alkylating Agents

(6) TABLE-US-00003 TABLE 3 Designation Source MeCl Methyl chloride DMS Dimethyl sulfate, Aldrich DES Diethyl sulfate, Aldrich
6.2 General Preparation Method of the Quaternary Ammonium Compounds:

Example E1

(7) 571 g (1.588 mol) of amine A1 were placed in a three-necked flask equipped with column, distillation system and stirrer motor and heated to 80° C. under a nitrogen atmosphere. To this were added 352.2 g (1.271 mol) of fatty acid FA 3 and 0.46 g of 50% aqueous hypophosphorous acid. A vacuum of 100 mbar was applied and the mixture was cautiously heated to 195° C., wherein water of reaction was collected in the outflow of the distillation system. After 2.5 hours, the vacuum was lowered to 20 mbar and further reacted for 1.5 hours. The condensation product thus obtained had an acid number of 0.9 mg KOH/g and an amine number of 96.2 mg KOH/g. The reaction mixture was cooled to 80° C. Over one hour, 186.2 g (1.477 mol) of dimethyl sulfate were added dropwise with stirring, wherein the temperature was maintained in a range of 80-95° C. Subsequently, 120 g of anhydrous ethanol were added and the mixture was further stirred at 80° C. for one hour. The quat mixture thus obtained had an amine number of 3.1 mg KOH/g.

(8) The further examples and comparative examples were carried out according to this procedure but with varied reactants or varied amount ratios—in each case as stated in tables 4 and 5 below.

(9) 6.3 Application Tests

(10) Table 4 specifies various inventive laundry and cleaning formulations by way of example. In each case, according to the procedure of 6.2, quat mixtures were prepared corresponding to the data in table 4, and were mixed with water such that each formulation resulted in 3% by weight quat mixture (calculated based on the solids content), 0.2% perfume oil, and water to 100%. The viscosity of the formulation obtained was determined in each case.

(11) TABLE-US-00004 TABLE 4 Moles of fatty acid Ex- Fatty Iodine per mole Alkylating Viscosity @ ample Amine acid number of amine agent 3% in mPas  E1 A1 FA3 <1.0 0.8 DMS 2400  E2 A1 FA3 <1.0 1.0 DMS 1000  E3 A1 FA3 <1.0 1.2 DMS 1060  E4 A1 FA1 18-22 0.8 DES 600  E5 A1 FA1 18-22 0.8 DMS 860  E6 A1 FA1 18-22 1.0 DMS 1080  E7 A1 FA1 18-22 1.2 DMS 580  E8 A1 FA2 30-42 1.0 DMS 590  E9 A3 FA1 18-22 1.0 DMS 770 E10 A3 FA3 <1.0 1.2 DMS 580 E11 A3 FA1 18-22 0.8 DMS 560 E12 A1 FA4 <2.0 0.8 DMS 1700

(12) For comparison, non-inventive examples are shown in table 5 in which: in V1 and V2, MeCl was used instead of DMS as alkylating agent in V3 to V6, the amine A2 substituted by R.sup.1 equals tallow having an iodine number of 18-22 was used instead of amine A3 substituted by R.sup.1 equals hydrogenated tallow having an iodine number of <1.0 in V7, an amine with a molar ratio of less than 0.8
was used.

(13) TABLE-US-00005 TABLE 5 Molar ratio moles of fatty acid Ex- Fatty per mole of Alkylating Viscosity @ ample Amine acid IN amine agent 3% in mPas V1 A1 FA3 <1.0 1.0 MeCl 130 V2 A1 FA1 18-22 1.0 MeCl 350 V3 A2 FA1 18-22 1.2 DMS 100 V4 A2 FA1 18-22 1.0 DMS 40 V5 A2 FA1 18-22 0.8 DMS 30 V6 A2 FA3 <1.0 1.0 DMS 315 V7 A1 FA3 <1.0 0.6 DMS 155

(14) The comparisons of V1 with E2 and of V2 with E6 show that the use of DMS instead of MeCl as alkylating agent contributes significantly to the solution to the problem of the present invention.

(15) The comparisons of V3 with E7, V4 with E6, V5 with E7 and V6 with E2 show that the use of radicals R.sup.1 with an iodine number of less than 10 instead of a radical R.sup.1 with a higher iodine number, at otherwise identical conditions, results in significantly higher viscosities.

(16) The comparison of V7 with E1 to E3 shows the influence of the molar ratio of fatty acid to amine. If this is too low, as in V7, an insufficient thickening effect is achieved.