COMPOSITION

Abstract

A N-acylated taurine composition comprising: (a) a first N-acylated taurine compound of the formula (IA) or a salt thereof:

##STR00001## and (b) a second N-acylated taurine compound of the formula (IB) or a salt thereof:

##STR00002## wherein R.sup.1a and R.sup.2a are C.sub.1-4 alkyl, wherein R.sup.1a and R.sup.2a are the same; R.sup.3 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.1-6 alkyl substituted with an aryl group; and R.sup.4 is C.sub.4-25 alkyl or C.sub.4-25 alkenyl, wherein the C.sub.4-25 alkyl or C.sub.4-25 alkenyl is optionally substituted by hydroxy.

Claims

1-11. (canceled)

12. A N-acylated taurine composition comprising: (a) a first N-acylated taurine compound of the formula (IA) or a salt thereof: ##STR00023## and (b) a second N-acylated taurine compound of the formula (IB) or a salt thereof: ##STR00024## wherein R.sup.1a and R.sup.2a are C.sub.1-4 alkyl, wherein R.sup.1a and R.sup.2a are the same; R.sup.3 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.1-6 alkyl substituted with an aryl group; and R.sup.4 is C.sub.4-25 alkyl or C.sub.4-25 alkenyl, wherein the C.sub.4-25 alkyl or C.sub.4-25 alkenyl is optionally substituted by hydroxy.

13. The N-acylated taurine composition according to claim 1, wherein: R.sup.1a and R.sup.2a are C.sub.1-2 alkyl wherein R.sup.1a and R.sup.2a are the same; R.sup.3 is C.sub.1-6 alkyl; and R.sup.4 is C.sub.8-18 alkyl or C.sub.8-18 alkenyl, wherein the C.sub.8-18 alkyl or C.sub.8-18 alkenyl is optionally substituted by hydroxy.

14. The N-acylated taurine composition according to claim 13, wherein R.sup.1a and R.sup.2a are methyl and/or R.sup.3 is C.sub.1-2 alkyl.

15. The N-acylated taurine composition according to claim 1, comprising the first N-acylated taurine compound of the formula (IA) or a salt thereof and the second N-acylated taurine compound of the formula (IB) or a salt thereof in a molar ratio of 99:1 to 1:99, for example 99:1 to 1:1, for example 99:1 to 4:1.

16. The N-acylated taurine composition according to claim 15, comprising the first N-acylated taurine compound of the formula (IA) or a salt thereof and the second N-acylated taurine compound of the formula (IB) or a salt thereof in a molar ratio of 99:1 to 1:1 or a molar ratio of 99:1 to 4:1.

17. A method of preparing the N-acylated taurine composition according to claim 1, the method comprising reacting a taurine composition comprising a first taurine compound of the formula (IIA) or a salt thereof and a second taurine compound of the formula (IIB) or a salt thereof: ##STR00025## with a fatty acid of the formula R.sup.4C(O)OH or a reactive derivative thereof, wherein R.sup.1a, R.sup.2a, R.sup.3 and R.sup.4 are each as defined in claim 12, to provide the N-acylated taurine composition.

18. The method according to claim 17, further comprising preparing the taurine composition by reacting an isethionic acid composition comprising a first isethionic acid compound of the formula (IIIA) or a salt thereof and a second isethionic acid compound of the formula (IIIb) or a salt thereof: ##STR00026## with a primary amine compound of the formula H.sub.2NR.sup.3, wherein R.sup.1a, R.sup.2a and R.sup.3 are each as defined in claim 12, to provide the taurine composition.

19. The method according to claim 18, further comprising preparing the isethionic acid composition by reacting a source of bisulfite anions with an alkylene oxide of the formula (IV): ##STR00027## wherein R.sup.5 is the same as R.sup.1a and R.sup.2a as defined in claim 12.

20. A N-acylated taurine compound of the formula (IC) or a salt thereof: ##STR00028## wherein: R.sup.1 and R.sup.2 are each independently selected from H or C.sub.1-4 alkyl, provided that one of R.sup.1 and R.sup.2 is H and the other of R.sup.1 and R.sup.2 is C.sub.1-4 alkyl; R.sup.3 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, or C.sub.1-6 alkyl substituted with an aryl group; and R.sup.4 is C.sub.4-25 alkyl or C.sub.4-25 alkenyl wherein the C.sub.4-25 alkyl or C.sub.4-25 alkenyl is optionally substituted by hydroxy.

21. The N-acylated taurine compound of the formula (IC) according to claim 20, wherein: R.sup.1 and R.sup.2 are each independently selected from H or C.sub.1-2 alkyl, provided that one of R.sup.1 and R.sup.2 is H and the other of R.sup.1 and R.sup.2 is C.sub.1-2 alkyl; R.sup.3 is C.sub.1-6 alkyl; and R.sup.4 is C.sub.8-18 alkyl or C.sub.8-18 alkenyl, wherein the C.sub.8-18 alkyl or C.sub.8-18 alkenyl is optionally substituted by hydroxy.

22. The N-acylated taurine compound of the formula (IC) according to claim 21 wherein R.sup.4 and R.sup.2 are each independently selected from H or methyl, provided that one of R.sup.4 and R.sup.2 is H and the other of R.sup.4 and R.sup.2 is methyl, and/or R.sup.3 is C.sub.1-2 alkyl.

23. A taurine composition comprising a first taurine compound of the formula (IIA) or a salt thereof and a second taurine compound of the formula (IIB) or a salt thereof: ##STR00029## wherein R.sup.1a and R.sup.2a are C.sub.1-4 alkyl, wherein R.sup.1a and R.sup.2a are the same; and R.sup.3 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.1-6 alkyl substituted with an aryl group.

24. A taurine composition according to claim 23, wherein: R.sup.1a and R.sup.2a are C.sub.1-2 alkyl, wherein R.sup.1a and R.sup.2a are the same; and R.sup.3 is C.sub.1-6 alkyl.

25. The taurine composition according to claim 24, wherein R.sup.1a and R.sup.2a are methyl and/or R.sup.3 is C.sub.1-2 alkyl.

26. Use of a composition according to claim 12 in the formulation of a personal care, home care, industrial or agricultural product.

27. Use of a compound according to claim 20 in the formulation of a personal care, home care, industrial or agricultural product.

28. A method of making a product formulation selected from the group consisting of a personal care, home care, industrial or agricultural product comprising the step of utilizing the composition of claim 1 as a component of said product formulation.

29. A method of making a product formulation selected from the group consisting of a personal care, home care, industrial or agricultural product comprising the step of utilizing the compound of claim 9 as a component of said product formulation.

Description

BRIEF DESCRIPTION OF THE FIGURES

[0152] For a better understanding of the invention, and to show how exemplary embodiments of the same may be carried into effect reference will be made, by way of example only, to the accompanying Figures, in which:

[0153] FIG. 1 shows the physical form of a sodium cocoyl N-methyl methyl taurate composition of Example 2 at ambient temperature and a concentration of 30.4 wt % active in water; and

[0154] FIG. 2 shows the physical form of sodium cocoyl N-methyl taurate of Example 3 at ambient temperature and a concentration of 30 to 31.5 wt % active in water.

[0155] The invention will now be further described with reference to the following non-limiting examples.

EXAMPLES

Example 1 (Inventive)Synthesis of Isomeric N-methyl Methyl Taurine Mixture

[0156] A 1 L stainless steel autoclave was fitted with overhead stirrer, thermocouple, pressure gauge and bursting disc. Sodium methyl isethionate (50 wt % solution in water, 156.3 g, 0.47 mol) and methylamine (40 wt % solution in water, 449.8 g, 5.79 mol) were charged. The autoclave was sealed and heated to 250 C. and held at this temperature for 5.5 hours. A pressure build-up of 90 bar was observed. After cooling to room temperature, the autoclave was vented. The reaction mass was discharged and concentrated on a rotary evaporator. After removal of excess methylamine, the vacuum was gradually increased to 125 mbar at a bath temperature of 70 C. to partially remove water. The partially concentrated product had an active material content of 60 wt %.

[0157] A sample of the reaction product was concentrated to dryness. .sup.1H and .sup.13C NMR analysis (D.sub.2O) of the dried product showed the sodium N-methyl methyl taurine product (isomeric mixture) as the major component. Based on NMR integration, the molar ratio of isomers was calculated as 97:3 (sodium 2-(methylammonium)propane-1-sulfonate to sodium 1-(methylammonium)propane-2-sulfonate).

Example 2 (Inventive)Synthesis of Isomeric Sodium Cocoyl N-methyl Methyl Taurate Mixture

[0158] A 1 L jacketed reactor was fitted with overhead stirrer, thermometer, pH probe and dropping funnel. N-methyl methyl taurine (60 wt % solution, 121.6 g, 0.416 mol) and water (238 g) were charged. Stirring was started and the reaction mass heated to 55 C. Cocoyl chloride (94.75 g, 0.43 mol) was charged over 3 hours via the dropping funnel; simultaneously the reaction pH was maintained in the range 9.5-10.5 by manual addition of 50 wt % aqueous NaOH solution (37 g overall). After completion of cocoyl chloride addition, the reaction temperature was increased to and held for 1 hour. The reaction mass was cooled to 50 C. and the pH adjusted to 7.8. Water was added to provide a final sodium cocoyl N-methyl methyl taurate content (mixture of isomers) of 30.4 wt %.

Example 3 (Comparative)Sodium Cocoyl N-methyl Taurate

[0159] A sample of sodium cocoyl N-methyl taurate (commercial name: Pureact WS Conc) was obtained. This material was prepared from N-methyl taurine in analogous manner to Example 2, and had an active content of 30-31.5 wt %.

Example 4Physical Form Comparison of Isomeric Sodium Cocoyl N-methyl methyl Taurate Mixture and Sodium Cocoyl N-methyl Taurate

[0160] The physical form of isomeric sodium cocoyl N-methyl methyl taurate mixture (Example 2) and sodium cocoyl N-methyl taurate (Example 3) were compared at ambient temperature, for the same active concentration.

[0161] The results are shown in Table 1.

TABLE-US-00001 TABLE 1 Physical form comparison of isomeric sodium cocoyl N-methyl methyl taurate mixture and sodium cocoyl N-methyl taurate Example 2 (inventive) 3 (comparative) Active content (wt %) 30.4 30-31.5 * Non volatiles (wt %) 40.9 38-43.0 * NaCl (wt %) 6.5 4-7 *.sup. Physical form @ 25 C. Clear, mobile liquid Thick, firm paste * commercial product specification

[0162] These results demonstrated a surprising advantage for the inventive product. As it is was liquid at ambient temperature, storage and handling was greatly improved and no pre heating would be required for transfer operations.

[0163] FIGS. 1 (Example 2, inventive) and 2 (Example 3, comparative) show the products at ambient temperature.

Example 5Physical Form of Isomeric Sodium Cocoyl N-methyl Methyl Taurate Mixture at Reduced Temperatures

[0164] This experiment was designed to simulate storage conditions in a cold warehouse.

[0165] A sample of the Example 2 product (100 g) was cooled in discrete steps. For each cooling step, the product was held for 30 minutes at that temperature, and the physical form of the product was visually inspected. The results are shown in Table 2.

TABLE-US-00002 TABLE 2 Physical form of Example 2 at reduced temperatures Temperature ( C.) Physical form 5 C. Clear, thin liquid 0 C. Clear, thin liquid 5 C. Clear liquid, becoming more viscous 10 C. Some solids apparent 15 C. Sample solidified

[0166] This experiment showed that inventive product of Example 2 remained fully liquid at temperatures as low as 5 C. This represents a significant advantage in commercial use as for most climates, the materials could be stored in non-temperature controlled warehousing.

[0167] The cooled Example 2 sample was then allowed to warm back to ambient temperature. The sample rapidly became fully liquid again, at a temperature of 8 C.

[0168] The present invention is not restricted to the details of the foregoing embodiment(s). The invention extends to any novel one, or any novel combination, of the features disclosed in this specification (including any accompanying claims, abstract and drawings), or to any novel one, or any novel combination, of the steps of any method or process so disclosed.