ESTERAMINE SALTS

Abstract

The present invention relates to an esteramine salt according to the general formula (I):

##STR00001##

The substituents R.sup.1, R.sup.2 and R.sup.3 are defined below.

The present invention further relates to a process for preparing such an esteramine salt according to general formula (I), wherein a corresponding monocarboxylic acid or an ester thereof are reacted with an aminoalcohol and an at least equimolar amount of a sulfonic acid.

Claims

1. Esteramine salt according to general formula (I) ##STR00010## wherein: R.sup.1 is C.sub.4-C.sub.30-alkyl or C.sub.4-C.sub.30-alkenyl, R.sup.2 is C.sub.3-C.sub.12-alkylene or —((CR.sup.10R.sup.11).sub.o—CR.sup.4R.sup.5—CR.sup.6R.sup.7—O).sub.m—(CR.sup.8R.sup.9).sub.n—, R.sup.3 is C.sub.2-C.sub.30-alkyl, C.sub.2-C.sub.30-alkenyl or unsubstituted or at least monosubstituted aryl and the substituents are independently selected from C.sub.1-C.sub.30-alkyl under the proviso that R.sup.3 is not para toluenyl, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently of each other selected from hydrogen or C.sub.1-C.sub.10-alkyl, m is an integer from 1 to 100, n is an integer from 2 to 12, and o is an integer from 0 to 10.

2. The esteramine salt according to claim 1, wherein R.sup.1 is C.sub.4-C.sub.30-alkyl, R.sup.2 is C.sub.3-C.sub.12-alkylene and R.sup.3 is C.sub.2-C.sub.30-alkyl or at least monosubstituted aryl and the substituents are independently selected from C.sub.1-C.sub.30-alkyl under the proviso that R.sup.3 is not para toluenyl.

3. The esteramine salt according to claim 1, wherein R.sup.1 is C.sub.6-C.sub.21-alkyl, R.sup.2 is C.sub.3-C.sub.6-alkylene and R.sup.3 is C.sub.6-C.sub.18-alkyl or at least monosubstituted phenyl and the substituents are independently selected from C.sub.1-C.sub.30-alkyl under the proviso that R.sup.3 is not para toluenyl.

4. The esteramine salt according to claim 1, wherein i) R.sup.1 is a mixture of at least two individual substituents and/or ii) R.sup.1 is unsubstituted straight-chain or branched C.sub.4-C.sub.30-alkyl or C.sub.4-C.sub.30-alkenyl.

5. The esteramine salt according to claim 1, wherein i) R.sup.3 is monosubstituted phenyl and the substituent is in para position and selected from C.sub.8-C.sub.16-alkyl, and/or ii) R.sup.3 is a mixture of at least two individual substituents.

6. The esteramine salt according to claim 1, wherein i) R.sup.2 is straight-chain C.sub.2-C.sub.12-alkylene, or ii) R.sup.2 is —(CH.sub.2—CHR.sup.7—O).sub.m—CH.sub.2—CHR.sup.9—, —(CHR.sup.11).sub.o—CHR.sup.5—CHR.sup.7—O—(CH.sub.2).sub.3— or —(CH.sub.2—CH.sub.2).sub.p—O—(CH.sub.2—CH.sub.2).sub.r—, R.sup.5, R.sup.7, R.sup.9 and R.sup.11 are independently of each other selected from H or methyl, m is an integer from 1 to 10, n is an integer from 2 to 6, o is an integer from 0 to 5, p is an integer from 1 to 3, is an integer from 1 to 3.

7. A process for preparing an esteramine salt according to claim 1, wherein a monocarboxylic acid or an ester thereof is reacted with an aminoalcohol and a sulfonic acid, and the molar ratio of sulfonic acid versus aminoalcohol is ≥1:1 [mol]/[mol].

8. The process according to claim 7, wherein i) the molar ratio of sulfonic acid versus aminoalcohol is from 1:1 to 2:1 [mol]/[mol], and/or ii) the molar ratio of carbonic acid or an ester thereof versus aminoalcohol is from 5:1 to 1:1 [mol]/[mol].

9. The process according to claim 7, comprising the steps a) to d) as follows: a) the monocarboxylic acid or an ester thereof is mixed with an aminoalcohol, b) the sulfonic acid is added afterwards, c) after completion of the addition of sulfonic acid, the reaction mixture is heated further, and d) formed water or formed alcohol is optionally distilled out of the reaction mixture.

10. The process according to claim 7, wherein the monocarboxylic acid has the general formula (IIa) ##STR00011## or an ester thereof has the general formula (IIb) ##STR00012## wherein R.sup.1 is C.sub.4-C.sub.30-alkyl or C.sub.4-C.sub.30-alkenyl, and R.sup.10 is C.sub.1-C.sub.30-alkyl, or R.sup.10 is a fragment of a triglyceride.

11. The process according to claim 7, wherein the aminoalcohol has the general formula (III)
HO—R.sup.2—NH.sub.2  (III) wherein R.sup.2 is C.sub.3-C.sub.12-alkylene or —((CR.sup.10R.sup.11).sub.o—CR.sup.4R.sup.5—CR.sup.6R.sup.7—O).sub.m—(CR.sup.8R.sup.9).sub.n—, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently of each other selected from hydrogen or C.sub.1-C.sub.10-alkyl, m is an integer from 1 to 100, n is an integer from 2 to 12, and o is an integer from 0 to 10.

12. The process according to claim 11, wherein i) the aminoalcohol according to formula (III) is selected from an aminoalcohol, wherein R.sup.2 is C.sub.3-C.sub.12-alkylene, or ii) the aminoalcohol according to formula (III) is selected from an aminoalcohol, wherein R.sup.2 is —((CR.sup.10R.sup.11).sub.o—CR.sup.4R.sup.5—CR.sup.6R.sup.7—O).sub.m—(CR.sup.8R.sup.9).sub.n— and R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently of each other selected from hydrogen or C.sub.1-C.sub.10-alkyl, m is an integer from 1 to 100, n is an integer from 2 to 12, and o is an integer from 0 to 10.

13. The process according to claim 7, wherein the sulfonic acid has the general formula (IV) ##STR00013## wherein R.sup.3 is C.sub.2-C.sub.30-alkyl, C.sub.2-C.sub.30-alkenyl or unsubstituted or at least monosubstituted aryl and the substituents are independently selected from C.sub.1-C.sub.30-alkyl under the proviso that R.sup.3 is not para toluenyl.

14. Use of the esteramine salt according to claim 1 in personal care, as curing agent for epoxy resins, as reactant in the production of polymers, in polyurethanes, polyureas, and as thermoplastic polyamide adhesives.

15. Use of the esteramine salt according to claim 14 in shampoo and body wash formulations.

16. A personal care composition comprising the esteramine salt according to claim 1.

Description

EXAMPLE 1: DECANOIC ACID, ESTER WITH 3-AMINO-1-PROPANOL AS DODECYLBENZENE SULFONIC ACID SALT

[0133] In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet, dropping funnel, and stirrer, 11.3 g 3-amino-1-propanol and 25.8 g decanoic acid are placed at room temperature to 42° C. To the mixture 51.5 g dodecylbenzene sulfonic acid (mixture of isomers wherein each isomer is based on a monosubstituted benzene sulfonic acid with the substituent in para position as shown in FIG. 4a) is added within 30 minutes. The temperature is allowed to rise to 80° C. during the addition. The reaction mixture is heated to 130° C. and is stirred for 4 hours at 130° C. Vacuum is applied (5 mbar) and the mixture is stirred for 16 hours at 130° C. 83.0 g of a brown viscous oil is obtained. .sup.1H-NMR in MeOD indicates 89% conversion to decanoic acid, ester with 3-amino-1-propanol as dodecylbenzene sulfonic acid salt.

EXAMPLE 2: DECANOIC ACID, ESTER WITH 3-AMINO-1-PROPANOL AS M-XYLENE SULFONIC ACID SALT

[0134] In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet, and stirrer, 18.77 g 3-amino-1-propanol and 43.07 g decanoic acid are placed at room temperature and heated to 55° C. To the mixture 46.66 g m-xylene sulfonic acid (2,4-dimethylbenzene sulfonic acid) is added in portions within 30 minutes. The temperature is allowed to rise to 70° C. during the addition. The reaction mixture is heated to 130° C. and is stirred for 4 hours at 130° C. Vacuum is applied (5 mbar) and the mixture is stirred for 30 hours at 130° C. 98.0 g of a brown wax is obtained. .sup.1H-NMR in MeOD indicates 81% conversion to decanoic acid, ester with 3-amino-1-propanol as xylene sulfonic acid salt.

EXAMPLE 3: 3,5,5-TRIMETHYLHEXANE ACID (ISONONANOIC ACID), ESTER WITH 3-AMINO-1-PROPANOL AS DODECYLBENZENE SULFONIC ACID SALT ACID SALT

[0135] In a 4-neck vessel with thermometer, distillation equipment, nitrogen inlet, dropping funnel, and stirrer, 15.02 g 3-amino-1-propanol and 31.65 g 3,5,5-trimethylhexane acid are placed at room temperature to 72° C. To the mixture 66.61 g dodecylbenzene sulfonic acid (mixture of isomers as described in example 1) is added within 1 hour. The temperature is allowed to rise to 65° C. during the addition. The reaction mixture is heated to 130° C. and is stirred for 4 hours at 130° C. The formed water is destilled off. Vacuum is applied (5 mbar) and the mixture is stirred for 22 hours at 138° C. 105.0 g of a brown viscous oil is obtained. .sup.1H-NMR in MeOD indicates 98% conversion to 3,5,5-trimethylhexane acid, ester with 3-amino-1-propanol as dodecylbenzene sulfonic acid salt.

EXAMPLE 4: DECANOIC ACID, ESTER WITH 2-(2-AMINOETHOXY)ETHANOL AS DODECYLBENZENE SULFONIC ACID SALT

[0136] In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet, dropping funnel, and stirrer, 26.3 g 2-(2-aminoethoxy)ethanol and 43.1 g decanoic acid are placed at room temperature. To the mixture 83.3 g dodecylbenzene sulfonic acid (mixture of isomers as described in example 1) is added within 15 minutes. The temperature is allowed to rise to 60° C. during the addition. The reaction mixture is heated to 130° C. and is stirred for 4 hours at 130° C. Vacuum is applied (5 mbar) and the mixture is stirred for 22 hours at 130° C. 140.0 g of a brown viscous oil is obtained. .sup.1H-NMR in MeOD indicates 95% conversion to decanoic acid, ester with 2-(2-aminoethoxy)ethanol as dodecylbenzene sulfonic acid salt.

EXAMPLE 5: 3,5,5-TRIMETHYLHEXANE ACID (ISONONANOIC ACID), ESTER WITH 2-(2-AMINOETHOXY)ETHANOL AS DODECYLBENZENE SULFONIC ACID SALT

[0137] In a 4-neck vessel with thermometer, reflux condenser, nitrogen inlet, dropping funnel, and stirrer, 26.3 g 2-(2-aminoethoxy)ethanol and 36.6 g 3,5,5-trimethylhexane acid are placed at room temperature. To the mixture 83.3 g dodecylbenzene sulfonic acid (mixture of isomers as described in example 1) is added within 15 minutes. The temperature is allowed to rise to 60° C. during the addition. The reaction mixture is heated to 130° C. and is stirred for 4 hours at 130° C. Vacuum is applied (350 mbar) and the mixture is stirred for 22 hours at 130° C. 142.0 g of a brown viscous oil is obtained. .sup.1H-NMR in MeOD indicates 90% conversion to 3,5,5-trimethylhexane acid, ester with 2-(2-aminoethoxy)ethanol as dodecylbenzene sulfonic acid salt.

EXAMPLE 6: C8-10 FATTY ACIDS, ESTER WITH 3-AMINO-1-PROPANOL AS DODECYLBENZENE SULFONIC ACID SALT, SYNTHESIZED FROM C8-10 FATTY ACID METHYL ESTER

[0138] In a 4-neck vessel with thermometer, distillation equipment, nitrogen inlet, dropping funnel, and stirrer, 3.8 g 3-amino-1-propanol and 26.6 g C8-10 fatty acid methyl ester (Aqnique ME610G) are placed at room temperature to 135° C. To the mixture 16.7 g dodecylbenzene sulfonic acid (mixture of isomers as described in example 1) is added within 30 minutes. The reaction mixture is stirred for 6 hours at 135° C., while the formed methanol is distilled off. Vacuum is applied (200 mbar) and the mixture is stirred for additional 5 hours at 135° C. and 200 mbar. Vacuum is lowered to 5 mbar and excess C8-10 fatty acid methyl ester is removed by stirring for 1.5 hours at 130° C. and 5 mbar. 27.0 g of a brown viscous oil is obtained. .sup.1H-NMR in MeOD indicates 94% conversion to C8-10 fatty acids, ester with 3-amino-1-propanol as dodecylbenzene sulfonic acid salt.

EXAMPLE 7: C8-10 FATTY ACIDS, ESTER WITH 5-AMINO-1-PENTANOL AS DODECYLBENZENE SULFONIC ACID SALT, SYNTHESIZED FROM C8-10 FATTY ACID METHYL ESTER

[0139] In a 4-neck vessel with thermometer, distillation equipment, nitrogen inlet, dropping funnel, and stirrer, 5.4 g 5-amino-1-pentanol and 26.6 g C8-10 fatty acid methyl ester (Aqnique ME610G) are placed at room temperature and are heated to 100° C. To the mixture 16.7 g dodecylbenzene sulfonic acid (mixture of isomers as described in example 1) is added within 10 minutes. The reaction mixture is stirred for 6 hours at 135° C., while the formed methanol is distilled off. Vacuum is applied (200 mbar) and the mixture is stirred for additional 6 hours at 135° C. and 200 mbar. Vacuum is lowered to 5 mbar and excess C8-10 fatty acid methyl ester is removed by stirring for 2 hours at 130° C. and 9 mbar. 28.0 g of a brown viscous oil is obtained. .sup.1H-NMR in MeOD indicates 83% conversion to C8-10 fatty acids, ester with 5-amino-1-pentanol as dodecylbenzene sulfonic acid salt.

EXAMPLE 8: OCTANOIC ACID, ESTER WITH 3-AMINO-1-PROPANOL AS DODECYLBENZENE SULFONIC ACID SALT, SYNTHESIZED FROM GLYCERYL TRIOCTANOATE

[0140] In a 4-neck vessel with thermometer, distillation equipment, nitrogen inlet, dropping funnel, and stirrer, 11.3 g 3-amino-1-propanol and 23.5 g glyceryltrioctanoate are placed at room temperature. To the mixture 50.0 g dodecylbenzene sulfonic acid (mixture of isomers as described in example 1) is added within 10 minutes. The reaction mixture is stirred for 12 hours at 135° C. 80.0 g of a brown viscous oil is obtained. .sup.1H-NMR in MeOD indicates 63% conversion to octanoic acid, ester with 3-amino-1-propanol as dodecylbenzene sulfonic acid salt.

COMPARATIVE EXAMPLE 1: 3,5,5-TRIMETHYLHEXANE ACID (ISONONANOIC ACID), ESTER WITH 3-AMINO-1-PROPANOL AS METHANE SULFONIC ACID SALT ACID SALT

[0141] In a 4-neck vessel with thermometer, distillation equipment, nitrogen inlet, dropping funnel, and stirrer, 22.5 g 3-amino-1-propanol are placed at room temperature. 47.5 g 3,5,5-trimethylhexane acid is added within 25 min. To the mixture 29.4 g methane sulfonic acid is added within 20 minutes. The temperature is allowed to rise to 60° C. during the addition. The reaction mixture is heated to 130° C. and is stirred for 4 hours at 130° C. The formed water is distilled off. Vacuum is applied (5 mbar) and the mixture is stirred for 22 hours at 135° C. 89.0 g of a brown solid is obtained. .sup.1H-NMR in MeOD indicates 91% conversion to 3,5,5-trimethylhexane acid, ester with 3-amino-1-propanol as methane sulfonic acid salt.

Use as Additives in Detergents

[0142] Technical stain swatches of blue knitted cotton containing Bacon Grease were purchased from Warwick Equest Ltd. The stains were washed for 30 min in a launder-o-meter (manufactured by SDL Atlas) at room temperature using per canister 500 mL of washing solution, 20 metal balls and ballast fabrics. The washing solution contained 5000 ppm (2.5 g in 500 mL canister) of detergent composition DC1 (table 1). Water hardness was 2.5 mM (Ca.sup.2+:Mg.sup.2+ was 4:1). 75 ppm of additives (as shown in table 2) were added to the washing solution of each canister separately and in the amount as detailed below. In the additive content is considered content of pure active in the salt.

[0143] Amount of additive is defined as follows:

[00001]$A=0.075\times \mathrm{weight}.Math..Math.\mathrm{of}.Math..Math.\mathrm{canister}.Math.\left[\mathrm{kg}\right]\times \frac{100}{\mathrm{content}.Math..Math.\mathrm{of}.Math..Math.\mathrm{active}.Math..Math.\mathrm{in}.Math..Math.\mathrm{salt}\left[\%\right]}$

[0144] After addition the pH value was re-adjusted to the pH value of washing solution without additive.

[0145] Standard colorimetric measurement was used to obtain L*, a* and b* values for each stain before and after the washing. From L*, a* and b* values the stain level were calculated as color difference ΔE (calculated according to DIN EN ISO 11664-4) between stain and untreated fabric.

[0146] Stain removal from the swatches was calculated as follows:

[00002]$\mathrm{Stain}.Math..Math.\mathrm{Removal}.Math..Math.\mathrm{Index}.Math..Math.\left(\mathrm{SRI}\right)=\frac{\Delta .Math..Math.E_{\mathrm{initial}}-\Delta .Math..Math.E_{\mathrm{washed}}}{\Delta .Math..Math.E_{\mathrm{initial}}}\times 100$$\Delta .Math..Math.E_{\mathrm{initial}}=\mathrm{Stain}.Math..Math.\mathrm{level}.Math..Math.\mathrm{before}.Math..Math.\mathrm{washing}.Math..Math.\Delta .Math..Math.E_{\mathrm{washed}}=\mathrm{Stain}.Math..Math.\mathrm{level}.Math..Math.\mathrm{after}.Math..Math.\mathrm{washing}$

[0147] Stain level corresponds to the amount of grease on the fabric. The stain level of the fabric before the washing (ΔE.sub.initial) is high, in the washing process stains are removed and the stain level after washing is smaller (ΔE.sub.washed). The better the stains have been removed the lower the value for ΔE.sub.washed will be and the higher the difference will be to ΔE.sub.initial. Therefore, the value of stain removal index increases with better washing performance as shown in table 2 below.

TABLE-US-00001 TABLE 1 Detergent composition DC1 Ingredients of liquid detergent percentage composition DC1 by weight n-C.sub.10-C.sub.13-alkylbenzene sulfonic acid 5.3 coconut C.sub.12-C.sub.18 fatty acid 2.4 sodium laureth sulfate + 2 EO 7.7 potassium hydroxide 2.2 C.sub.13C.sub.15- oxo alcohol + 7 EO 5.4 1,2 propylene glycol 6 ethanol 2 water To Balance pH of detergent composition DC1 = 8.0

TABLE-US-00002 TABLE 2 Results of strain removal employing detergent composition DC1 and additives SRI, Bacon additives Grease # to DC1 name and amount of additive Cleaning 1 none 28.4 2 Example 1 3-Amino-1-propanol, ester with 44.2 decanoic acid, 4-dodecylbenzene sulfonic acid (mixture of isomers) salt, 0.101 g per wash 3 Example 3 3-Amino-1-propanol, ester with 43.5 3,5,5-trimethylhexanoic acid, 4-dodecylbenzene sulfonic acid (mixture of isomers) salt, 0.095 g per wash 4 Comparative 3-Amino-1-propanol, ester with 38.4 Example 1 3,5,5-trimethylhexanoic acid, methanesulfonic acid salt, 0.059 g per wash

[0148] As can be seen from table 2, especially form the comparison of experiments #3 and 4, strains can be removed more efficiently by employing a detergent composition DC1 containing a compound according to the present invention (example 3) compared to a composition containing comparative example 1 instead.