Composition

Abstract

The present invention provides an N-acylated taurine composition comprising (a) a first N-acylated taurine compound of formula (IA) or a salt thereof and (b) a second N-acylated taurine compound of formula (IB) or a salt thereof (wherein R 1a and R 2a are C 1-4 alkyl, R 1a and R 2a are the same, R 3 is C 1-6 alkyl, C 2-6 alkenyl or C 1-6 alkyl substituted with an aryl group, and R 4 is C 4-25 alkyl or C 4-25 alkenyl, and C 4-25 alkyl or C 4-25 alkenyl may be substituted by hydroxy). 【Chemical Formula 1】 JPEG2025524946000031.jpg73170

Description

Technical Field

[0001] The present invention relates to an N-acylated taurine composition and a method for preparing an N-acylated taurine composition. The N-acylated taurine composition comprises a mixture of isomers of an N-acylated taurine compound. The present invention also provides an N-acylated taurine compound and a taurine composition. The N-acylated taurine composition and compound can be useful for a wide range of applications.

Background Art

[0002] Taurate compounds (such as N-methyltaurate compounds) are known as anionic surfactants and are widely used in a variety of applications as foaming agents and detergents. Such applications include personal care, home care, industrial, and agricultural uses. Taurate compounds are also hydrolytically stable over a wide pH range, for example, a pH range of 2 to 13. This hydrolytic stability makes taurate compounds desirable for use in applications that require stability over a wide range of pH values.

[0003] Taurate compounds are typically provided as a soft or firm paste or a viscous liquid and thus require storage in a warm room and / or heating before use. This makes it difficult and costly to store and / or handle the compound, especially on a large scale.

Summary of the Invention

Problems to be Solved by the Invention

[0004] Therefore, there is a need for alternative taurate-type compounds and compositions that provide the advantageous properties of known taurate compounds but are easier to store and / or handle at ambient temperature.

Means for Solving the Problems

[0005] According to a first aspect of the present invention, (a) Formula (IA)

Chemical Formula

[0006] According to a second aspect of the present invention, there is provided a method for preparing an N-acylated taurine composition based on the first aspect, comprising reacting a taurine composition containing a first taurine compound of formula (IIA) or a salt thereof and a second taurine compound of formula (IIB) or a salt thereof [Chemical formula] with a fatty acid of formula R -C(O)OH or a reactive derivative thereof to produce an N-acylated taurine composition, wherein R 4 , R 1a , R 2a , R 3 and R 4 are as defined in the first aspect of the present invention, respectively.

[0007] According to a third aspect of the present invention, formula (IC) [Chemical formula] (In the formula, R 1 and R 2 are each independently H or C 1-4 alkyl, provided that R 1 and R 2 one of them is H and the other is C 1-4 alkyl, R 3 is C 1-6 alkyl, C 2-6 alkenyl, or C alkyl substituted with an aryl group 1-6 alkyl, and R 4 is C 4-25 alkyl or C 4-25 alkenyl, and C 4-25 alkyl or C 4-25 alkenyl may be substituted by hydroxy), an N-acylated taurine compound or a salt thereof is provided.

[0008] According to a fourth aspect of the present invention, a first taurine compound of formula (IIA) or a salt thereof and a second taurine compound of formula (IIB) or a salt thereof [Chemical formula] (In the formula R 1a and R 2a are C 1-4 alkyl, R 1a and R 2a are the same, and R 3 is C 1-6 alkyl, C 2-6 alkenyl or C alkyl substituted with an aryl group 1-6 alkyl), a taurine composition containing the same is provided. [Brief Description of the Drawings]

[0009] To better understand the present invention and to illustrate how exemplary embodiments of the present invention can be implemented, as an example only, figures are attached.

Figure 1

Figure 2

DETAILED DESCRIPTION OF THE INVENTION

[0010] Unless otherwise specified, the following terms used in this specification and the claims have the meanings set forth below.

[0011] The terms "alkyl" and "alkenyl" each include both straight-chain and branched-chain alkyl and alkenyl groups.

[0012] As used herein, the term "aryl" relates to an organic radical formed by removing one hydrogen from an aromatic hydrocarbon and includes any monocyclic, bicyclic or polycyclic carbocyclic ring of up to 7 members in each ring, with at least one ring being aromatic.

[0013] As used in this specification and the appended claims, the singular forms "a", "an" and "the" include both singular and plural referents unless the context clearly dictates otherwise.

[0014] Throughout this specification, the term "comprising" or "comprises" means including the specified component(s) but not excluding the presence of other components. The term "consisting essentially of" or "consists essentially of" means including the specified component, but excluding other components except for those added for purposes other than achieving the technical effects of the present invention. The term "consisting of" or "consists of" means including the specified component but excluding other components.

[0015] Whenever appropriate and depending on the context, the use of the term "comprises" or "comprising" may be construed to include the meaning "consists essentially of" or "consisting essentially of", and may also be construed to include the meaning "consists of" or "consisting of".

[0016] As used herein, unless otherwise specified, all numbers such as those representing values, ranges, amounts, or percentages, even when the word "about" is not explicitly indicated, may be read as if preceded by the word "about".

[0017] The recitation of a numerical range by endpoints includes all integers and, where appropriate, fractions included within that range (e.g., 1 to 5 can include, for example, 1, 2, 3, 4 when referring to the number of elements, and can also include 1.5, 2, 2.75, and 3.80 when referring to measured values). The recitation of endpoints includes the endpoint values themselves (e.g., 1.0 to 5.0 includes both 1.0 and 5.0). Any numerical range described herein is intended to include all sub-ranges subsumed therein.

[0018] Any optional features described in this specification can be used individually or in combination with each other, where appropriate, and in particular in the combinations described in the appended claims. The optional features of each exemplary aspect of the invention described herein are also applicable, where appropriate, to any other aspect or exemplary aspect of the invention. In other words, those skilled in the art reading this specification should consider the optional features of each aspect or embodiment of the invention to be interchangeable and combinable between different aspects of the invention.

[0019] As used herein, the term "and / or" means that when used in a listing of two or more items, any one of the listed items can be used alone, or any combination of two or more of the listed items can be used. For example, if the listing is described as including group A, B, and / or C, the listing may include A alone; B alone; C alone; a combination of A and B; a combination of A and C; a combination of B and C; or a combination of A, B, and C.

[0020] According to a first aspect of the invention, (a) a first N-acylated taurine compound of formula (IA)

Chemical formula

Chemical formula

[0021] The N-acylated taurine composition of the first aspect of the present invention is advantageously a liquid that is fluid, pumpable and / or injectable at ambient temperature and usually at temperatures below ambient temperature such as below 10°C, for example below 5°C or below 0°C. The N-acylated taurine composition of the first aspect of the present invention is advantageously a liquid that is fluid, pumpable and / or injectable at temperatures above -10°C and below ambient temperature. Therefore, the N-acylated taurine composition of the first aspect of the present invention is easy to handle, store and compound.

[0022] The N-acylated taurine composition of the first aspect of the present invention is usually advantageously a substantially transparent or transparent liquid at ambient temperature and usually at temperatures below ambient temperature such as below 10°C, for example below 5°C or below 0°C. The N-acylated taurine composition of the first aspect of the present invention is usually advantageously a substantially transparent or transparent liquid at temperatures above -10°C and below ambient temperature. Therefore, the N-acylated taurine composition of the first aspect of the present invention does not impart discoloration or cloudiness to other compositions when used in combination.

[0023] Since the first and second N-acylated taurine compounds (or their salts) in the N-acylated taurine composition of the first aspect of the present invention are structural isomers, the N-acylated taurine composition of the first aspect of the present invention is an isomer composition.

[0024] R in the compounds of formula (IA) and (IB) or their salts 1a and R 2a are C 1-4 alkyl, and R 1a and R 2a are the same. Suitably, R 1a and R 2a are C 1-2is alkyl, R 1a and R 2a are the same. Preferably, R 1a and R 2a are both methyl.

[0025] R in the compounds of formula (IA) and (IB) or their salts 3 is C 1-6 alkyl, C 2-6 alkenyl or C 1-6 alkyl substituted with an aryl group. Suitably, R 3 is C 1-6 alkyl or C 2-6 alkenyl. More suitably, R 3 is C 1-6 alkyl, for example C 1-2 alkyl. Preferably, R 3 is methyl.

[0026] R in the compounds of formula (IA) and (IB) or their salts 4 is C 4-25 alkyl or C 4-25 alkenyl, and C 4-25 alkyl or C 4-25 alkenyl may be substituted by hydroxy. Suitably, R 4 is C 4-25 alkyl, for example C 8-18 alkyl, and C 4-25 alkyl, for example C 8-18 alkyl may be substituted by hydroxy. Suitably, R 4 is unsubstituted C 4-25 alkyl, for example unsubstituted C 8-18 alkyl.

[0027] R as defined herein 4 is C 4-25 alkyl or C 4-25 alkenyl groups, for example when these groups are derived from natural sources, may be included. Examples of suitable natural sources include fatty acid mixtures obtained directly from coconut oil or palm kernel oil, or hydrogenated (for example unsaturated C 18(for reducing the amount of the compound) or “topping” (i.e., distillation of the bulk fatty acid mixture for reducing the level of C8 and / or C 10 Examples include fatty acid mixtures obtained after treatment steps such as

[0028] Suitable salts of the compounds of formulas (IA) and (IB) include any appropriate salts. For example, salts of the compounds of formulas (IA) and (IB) are salts (IA’) and (IB’) as follows [Chemical formula] (wherein R 1a , R 2a , R 3 and R 4 are as defined herein, m is 1 or 2, and X m+ is any suitable cation that provides charge neutrality, such as an alkali metal or alkaline earth metal cation (e.g., sodium, potassium, lithium, calcium or magnesium cation) or an ammonium or substituted ammonium cation (e.g., dimethylammonium or tetra-n-butylammonium cation), and may be in the form of + Preferably, X

[0029] The salts of N-acylated taurine compounds are also known as taurinates.

[0030] A first aspect of the present invention is R 1a and R 2a are C 1-2 alkyl (e.g., methyl), R 1a and R 2a are the same, R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, C 8-18 alkyl or C 8-18An alkenyl may be substituted by hydroxy, and an N-acylated taurine composition can be provided.

[0031] The first aspect of the present invention is R 1a and R 2a are both methyl, R 3 is C 1-2 alkyl (e.g., methyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl may be substituted by hydroxy, and an N-acylated taurine composition can be provided.

[0032] The first aspect of the present invention is R 1a and R 2a is C 1-2 alkyl (e.g., methyl), R 1a and R 2a are the same, R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl is unsubstituted, and an N-acylated taurine composition can be provided.

[0033] The first aspect of the present invention is R 1a and R 2a are both methyl, R 3 is C 1-2 alkyl (e.g., methyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18Alkyl or C 8-18 An N-acylated taurine composition can be provided in which the alkenyl is unsubstituted.

[0034] The N-acylated taurine composition of the first aspect of the present invention may contain N-acylated taurine compounds (or their salts) of formulas (IA) and (IB) in any suitable ratio. For example, the N-acylated taurine composition may contain a first N-acylated taurine compound or its salt of formula (IA) and a second N-acylated taurine compound or its salt of formula (IB) in a molar ratio of 99:1 to 1:99, for example 99:1 to 1:1. Preferred ratios may be, for example, 99:1 to 4:1 or 9:1 to 4:1. Other preferred ratios may be 85:15 or 97:3.

[0035] According to a second aspect of the present invention, there is provided a method for preparing an N-acylated taurine composition according to the first aspect of the present invention, which comprises a first taurine compound of formula (IIA) or its salt and a second taurine compound of formula (IIB) or its salt

Chemical formula

[0036] Since the first taurine compound of formula (IIA) and the second taurine compound of formula (IIB) (or salts thereof) in the taurine composition are structural isomers, this represents a mixture of isomers (taurine). For example, the taurine composition may contain the first taurine compound of formula (IIA) and the second taurine compound of formula (IIB) (or salts thereof) in a molar ratio of 99:1 to 1:99, such as 99:1 to 1:1. Preferred ratios may be, for example, 99:1 to 4:1 or 9:1 to 4:1. Other preferred ratios may be 85:15 or 97:3.

[0037] The taurine composition is reacted with a fatty acid of the formula R 4 -C(O)OH or a reactive derivative thereof under any suitable reaction conditions, where R 1a , R 2a , R 3 and R 4 are as defined herein. This reaction can be carried out under any suitable reaction conditions, which is determined by the specific reagents used.

[0038] For example, when reacting the taurine composition with a fatty acid of the formula R 4 -C(O)OH, a suitable reaction temperature is 160 - 230 °C. In this case, the reaction may be carried out in the presence of a suitable catalyst. Suitable catalysts will be well known to those skilled in the art.

[0039] When reacting the taurine composition with a reactive derivative of a fatty acid of the formula R 4 -C(O)Cl such as R 4 -C(O)OH, a suitable reaction temperature is 45 - 75 °C, such as 50 - 65 °C.

[0040] Any suitable reaction solvent such as water or alcohol, preferably water, may be used. The reaction is usually carried out at a pH of 9.5 - 10.5, which can be maintained by the addition of a suitable base such as sodium hydroxide or by the addition of a suitable buffer.

[0041] The method according to the second aspect of the present invention may further include a step of preparing a taurine composition by reacting an isethionic acid composition containing a first isethionic acid compound of formula (IIIA) or a salt thereof and a second isethionic acid compound of formula (IIIB) or a salt thereof with

Chemical formula

[0042] The salts of the compounds of formulas (IIIA) and (IIIB) include any suitable salts. For example, the salts of the compounds of formulas (IIIA) and (IIIB) are salts (IIIA’) and (IIIB’) as follows

Chemical formula

[0043] Therefore, the method for preparing an N-acylated taurine composition according to the first aspect of the present invention is (1) an isethionic acid composition containing a first isethionic acid compound (IIIA) or a salt thereof and a second isethionic acid compound (IIIB) or a salt thereof

Chemical formula

[0044] Since the first isethionic acid compound (IIIA) and the second isethionic acid compound (IIIB) (or salts thereof) in the isethionic acid composition are structural isomers, this represents a mixture of isomers (isethionic acid). The normal molar ratio of the first isethionic acid compound (IIIA) and the second isethionic acid compound (IIIB) (or salts thereof) in the isethionic acid composition may be in the range of 99:1 to 1:1, for example, 99:1 to 4:1.

[0045] Isethionic acid compositions containing the first isethionic acid compound (IIIA) or a salt thereof and the second isethionic acid compound (IIIB) or a salt thereof are well known and can be obtained by any suitable means described, for example, in US 8105993. Usually, the isethionic acid composition is prepared and / or supplied as a mixture of isomers and reacted without separating the isomers.

[0046] For example, an isethionic acid composition containing the first isethionic acid compound (IIIA) or a salt thereof and the second isethionic acid compound (IIIB) or a salt thereof is obtained from a source of bisulfite anions, such as a compound of formula HO-S(O)-O - X + to a compound of formula (IV) [Chemical formula] (wherein R 5 is the same as R 1a and R 2a , and X + is a cation as defined herein (for example, m is 1 in the formula)), and can be prepared by reacting with an alkylene oxide. This reaction can be carried out under any suitable reaction conditions known to those skilled in the art. For example, the reaction can be carried out at a pH of 4 to 10, such as 5 to 10, for example, about 7. The reaction can be carried out at a temperature of 20 to 200 °C, such as 30 to 95 °C, for example, 50 to 80 °C. The reaction can be carried out at a pressure of 0 to 0.7 mPa, such as 0.07 to 0.3 mPa.

[0047] The isethionic acid composition can be reacted with a primary amine under any suitable reaction conditions. Suitable reaction temperatures are 200 to 280 °C, such as 220 to 260 °C. Any suitable reaction solvent such as water and / or an aliphatic alcohol, preferably water, may be used.

[0048] The method according to the second aspect of the present invention may include a step of removing an excess primary amine compound of the formula H2NR 3 from the reaction product, such as after the reaction between the isethionic acid composition and the primary amine is completed.

[0049] According to a third aspect of the present invention, the formula (IC)

Chemical formula

[0050] In the compound of formula (IC) or a salt thereof, R 1 and R 2 are selected from H and C 1-4 alkyl, provided that R 1 and R 2 one of them is H and the other is C 1-4 alkyl. Appropriately, R 1 and R 2 one of them is C 1-4 alkyl and the other is H. Appropriately, R 1 and R 2 one of them is C 1-2 alkyl and the other is H. Appropriately, R 1 and R 2 one of them is methyl and the other is H.

[0051] In one embodiment, in the compound of formula (IC) or a salt thereof, R 1 is C 1-4 alkyl and R 2 is H. Appropriately, R 1 is C 1-2 alkyl and R 2 is H. Appropriately, R 1 is methyl and R 2 is H.

[0052] In one embodiment, in the compound of formula (IC) or a salt thereof, R 2 is C 1-4 alkyl and R 1 is H. Appropriately, R 2 is C 1-2 alkyl and R 1 is H. Appropriately, R 2 is methyl and R 1 is H.

[0053] R in the compound of formula (IC) or a salt thereof 3 is C 1-6 Alkyl, C 2-6 C substituted with alkenyl or aryl groups 1-6 Suitably, R 3 is C 1-6 Alkyl or C 2-6 More suitably, R is alkenyl. 3 is C 1-6 Alkyl, e.g., C 1-2 Preferably, R 3 is methyl.

[0054] R in the compound of formula (IC) or a salt thereof 4 is C 4-25 Alkyl or C 4-25 alkenyl, C 4-25 Alkyl or C 4-25 The alkenyl may be substituted by hydroxy. Suitably, R 4 is C 8-18 Alkyl or C 8-18 alkenyl, C 8-18 Alkyl or C 8-18 The alkenyl may be substituted by hydroxy. Suitably, R in the compound of formula (IC) 4 is unsubstituted C 8-18 Alkyl or unsubstituted C 8-18 It is alkenyl.

[0055] R in the compound of formula (IC) or a salt thereof 4 is C 4-25 Alkyl, e.g., C 8-18 may be alkyl, C 4-25 Alkyl or C 8-18 The alkyl may be substituted by hydroxy. Suitably, R in the compound of formula (IC) 4 is unsubstituted C 4-25 Alkyl, e.g., unsubstituted C 8-18 It may also be alkyl.

[0056] The salts of the compound of formula (IC) include any suitable salts. For example, the salts of the compound of formula (IC) are salts (IC’) as follows [Chemical formula] (wherein R 1 , R 2 , R 3 and R 4 are each as defined herein, m is 1 or 2, and X m+ is any suitable cation that provides charge neutrality, such as an alkali metal or alkaline earth metal cation (e.g., sodium, potassium, lithium, calcium or magnesium cation) or an ammonium or substituted ammonium cation (e.g., dimethylammonium or tetra-n-butylammonium cation), and may be in the form of). Preferably, X + is a sodium cation.

[0057] The third aspect of the present invention is R 1 and R 2 are each independently selected from H or C 1-2 alkyl (e.g., methyl), provided that one of R 1 and R 2 is H and the other is C 1-2 alkyl, R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl may be substituted by hydroxy, and an N-acylated taurine compound of formula (IC) or a salt thereof can be provided.

[0058] The third aspect of the present invention is R 1 is C 1-4 alkyl, R 2 is H, R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl may be substituted by hydroxy, and an N-acylated taurine compound of formula (IC) or a salt thereof can be provided.

[0059] A third aspect of the present invention is R 1 is C 1-2 alkyl, R 2 is H, and R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl may be substituted by hydroxy, and an N-acylated taurine compound of formula (IC) or a salt thereof can be provided.

[0060] A third aspect of the present invention is R 1 is methyl, R 2 is H, and R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl may be substituted by hydroxy, and an N-acylated taurine compound of formula (IC) or a salt thereof can be provided.

[0061] A third aspect of the present invention is R 2 is C 1-4 alkyl, and R 1 is H, R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl may be substituted by hydroxy, and an N-acylated taurine compound of formula (IC) or a salt thereof can be provided.

[0062] The third aspect of the present invention is R 2 is C 1-2 alkyl, and R 1 is H, R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18 alkenyl may be substituted by hydroxy, and an N-acylated taurine compound of formula (IC) or a salt thereof can be provided.

[0063] The third aspect of the present invention is R 2 is methyl, and R 1 is H, R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), and R 4 is C 8-18 alkyl or C 8-18 alkenyl, and C 8-18 alkyl or C 8-18An alkenyl may be substituted by hydroxy, and an N-acylated taurine compound of formula (IC) or a salt thereof can be provided.

[0064] The N-acylated taurine compound of the third aspect of the present invention can be prepared by any suitable method. For example, the N-acylated taurine compound can be isolated from the N-acylated taurine composition based on the first aspect of the present invention, that is, it is possible by isolating the compound from the composition. The N-acylated taurine compound can be prepared from a suitable taurine compound (for example, isolated from the taurine composition defined herein) by reaction with a fatty acid or a reactive derivative thereof as defined herein.

[0065] According to the fourth aspect of the present invention, a first taurine compound of formula (IIA) or a salt thereof and a second taurine compound of formula (IIB) or a salt thereof

Chemical formula

[0066] Since the first and second taurine compounds in the taurine composition of the fourth aspect of the present invention are structural isomers, the taurine composition of the fourth aspect of the present invention is an isomer (taurine) composition.

[0067] R 1a and R 2a in the compounds (or their salts) of formulas (IIA) and (IIB) are C 1-4 alkyl, R 1a and R 2ais the same. Appropriately, R 1a and R 2a are C 1-2 alkyl, and R 1a and R 2a are the same. Preferably, R 1a and R 2a are both methyl.

[0068] R in the compounds of formula (IIA) and (IIB) (or their salts) 3 is C 1-6 alkyl, C 2-6 alkenyl or C 1-6 alkyl substituted with an aryl group. Appropriately, R 3 is C 1-6 alkyl or C 2-6 alkenyl. More appropriately, R 3 is C 1-6 alkyl, for example C 1-2 alkyl. Preferably, R 3 is methyl.

[0069] The mention of salts of the compounds of formula (IIA) and (IIB) includes any suitable salts.

[0070] For example, under basic conditions, the salts of the compounds of formula (IIA) and (IIB) are sulfonate salts (IIA') and (IIB') as follows

Chemical formula

[0071] For example, under acidic conditions, the salts of the compounds of formula (IIA) and (IIB) may be in the form of ammonium salts (IIA”) and (IIB”) as follows

Chemical formula

[0072] For example, at the isoelectric point, the salts of the compounds of formula (IIA) and (IIB) may be in the zwitterionic form (also called an inner salt or internal salt). For example, the salts of the compounds of formula (IIA) and (IIB) may be zwitterions (IIA’’’) and (IIIB’’’) as follows

Chemical formula

[0073] A fourth aspect of the present invention is R 1a and R 2a are C 1-2 alkyl (e.g., methyl), R 1a and R 2a are the same, and R 3 is C 1-6 alkyl (e.g., C 1-2 alkyl), a taurine composition can be provided.

[0074] A fourth aspect of the present invention is R 1a and R 2a are both methyl, and R 3 is C 1-2It is possible to provide a taurine composition that is alkyl (for example, methyl).

[0075] The taurine composition of the fourth aspect of the present invention may contain the taurine compounds of formulas (IIA) and (IIB) (or salts thereof) in any suitable ratio. For example, the taurine composition may contain a first taurine compound of formula (IIA) or a salt thereof and a second taurine compound of formula (IIB) or a salt thereof in a molar ratio of 99:1 to 1:99, for example, 99:1 to 1:1. Preferred ratios may be, for example, 99:1 to 4:1 or 9:1 to 4:1. Other preferred ratios may be 85:15 or 97:3.

[0076] The taurine composition of the fourth aspect of the present invention can be prepared by any suitable method, for example, by reacting an isethionate composition containing a first isethionic acid compound of formula (IIIA) and a second isethionic acid compound of formula (IIIB) (or salts thereof) with a primary amine compound of formula H2NR 3 as defined herein with respect to the second aspect of the present invention.

[0077] The composition of the first aspect of the present invention and the compound of the third aspect of the present invention may be useful for various applications. The present invention further provides the use of the composition according to the first aspect of the present invention or the compound according to the third aspect of the present invention in the formulations of personal care, home care, industrial or agricultural products.

[0078] Next, the present invention will be further described with respect to the following examples. However, the present invention is not limited to these examples. [Examples]

Examples

[0079] (The present invention) - Synthesis of isomer N - methylmethyltaurine mixture An overhead stirrer, a thermocouple, a pressure gauge, and a bursting disc were attached to a 1 L stainless steel autoclave. Sodium methyl isethionate (50 wt% aqueous solution, 156.3 g, 0.47 mol) and methylamine (40 wt% aqueous solution, 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. An increase in pressure of approximately 90 bar was observed. After cooling to room temperature, the autoclave was vented. The reaction product was removed and concentrated on a rotary evaporator. After removing the excess methylamine, the bath temperature was 70 °C and the vacuum was gradually increased to 125 mbar to partially remove water. The partially concentrated product had an active substance content of 60 wt%.

[0080] A sample of the reaction product was concentrated and dried. The 1 H and 13 C NMR analysis (D2O) showed that the main component was sodium N-methylmethyltaurine product (isomer mixture). Based on the NMR integration values, the molar ratio of the isomers was calculated to be 97:3 (sodium 2-(methylammonium)propane-1-sulfonate vs sodium 1-(methylammonium)propane-2-sulfonate).

Example

[0081] (The present invention) - Synthesis of an isomer cocoyl N-methylmethyltaurine sodium mixture An overhead stirrer, thermometer, pH probe, and dropping funnel were attached to a 1 L jacketed reactor. N-Methylmethyltaurine (60 wt% solution, 121.6 g, 0.416 mol) and water (238 g) were charged. Stirring was started and the reactants were heated to 55 °C. Cocoyl chloride (94.75 g, 0.43 mol) was added via the dropping funnel over 3 hours; simultaneously, the reaction pH was maintained in the range of 9.5 - 10.5 by manually adding a 50 wt% aqueous NaOH solution (37 g in total). After the addition of cocoyl chloride was complete, the reaction temperature was raised to 65 °C and held for 1 hour. The reaction mixture was cooled to 50 °C and the pH was adjusted to 7.8. Water was added to give a final sodium cocoyl N-methylmethyltaurinate content (mixture of isomers) of 30.4 wt%.

Example

[0082] (Comparative Example) - Sodium cocoyl N-methyltaurinate A sample of sodium cocoyl N-methyltaurinate (trade name: Pureact® WS Conc) was obtained. This substance was prepared from N-methyltaurine in the same manner as in Example 2 and had an active content of 30 - 31.5 wt%.

Example

[0083] Comparison of the physical forms of the isomeric sodium cocoyl N-methylmethyltaurinate mixture and sodium cocoyl N-methyltaurinate The physical forms of the isomeric sodium cocoyl N-methylmethyltaurinate mixture (Example 2) and sodium cocoyl N-methyltaurinate (Example 3) were compared at ambient temperature with respect to the same active concentration.

[0084] The results are shown in Table 1.

Table 1

[0085] These results demonstrated the surprising advantages of the products of the present invention. Since they were liquid at ambient temperature, storage and handling were significantly improved and no preheating was required for transfer operations.

[0086] Figure 1 (Example 2, the present invention) and Figure 2 (Example 3, comparison) show the products at ambient temperature.

Examples

[0087] Physical form of the isomer cocoyl N-methyl methyl taurate mixture at low temperature This experiment was designed to simulate storage conditions in a chilled warehouse.

[0088] A sample (100 g) of the product of Example 2 was cooled in discontinuous steps. At each cooling step, the product was held at that temperature for 30 minutes and the physical form of the product was visually inspected. The results are shown in Table 2.

Table 2

[0089] This experiment showed that the product of the present invention of Example 2 remained completely liquid at temperatures as low as about -5°C. This allows storage in warehouses with unregulated temperatures for most climates, which is a significant advantage in commercial applications.

[0090] Next, the cooled sample of Example 2 was reheated to ambient temperature. The sample rapidly became completely liquid again at a temperature of -8°C.

[0091] The present invention is not limited to the details of the foregoing embodiments. The present invention extends to any novel or novel combination of the features disclosed in this specification (including the appended claims, abstract, and drawings), or to any novel or novel combination of the steps of the methods or processes similarly disclosed.

Claims

1. (a) A first N-acylated taurine compound of formula (IA) 【Chemical 1】 or a salt thereof and (b) A second N-acylated taurine compound of formula (IB) 【Chemical 2】 or a salt thereof (wherein R １ａ and R ２ａ is C １－４ alkyl, and R １ａ and R ２ａ are the same, R ３ is C １－６ alkyl, C ２－６ alkyl substituted with an alkenyl or aryl group, and １－６ is alkyl, and R ４ is C ４－２５ alkyl or C ４－２５ alkenyl, and the C ４－２５ alkyl or C ４－２５ alkenyl may be substituted by hydroxy), and an N-acylated taurine composition.

2. R １ａ and R ２ａ is C １－２ alkyl (e.g., methyl), and R １ａ and R ２ａ are the same, R ３ is C １－６ alkyl (e.g., C １－２ alkyl), and R ４ is C ８－１８ alkyl or C ８－１８ alkenyl, and the C ８－１８ alkyl or C ８－１８ alkenyl may be substituted by hydroxy. The N-acylated taurine composition according to claim 1.

3. The N-acylated taurine composition according to Claim 1 or 2, comprising the first N-acylated taurine compound of formula (IA) or a salt thereof and the second N-acylated taurine compound of 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.

4. A taurine composition comprising a first taurine compound of formula (IIA) or a salt thereof and a second taurine compound of formula (IIB) or a salt thereof [Chemical Formula 3] is Formula R ４ reacting with a fatty acid of the formula -C(O)OH or a reactive derivative thereof to produce an N-acylated taurine composition, wherein R １ａ , R ２ａ , R ３ and R ４ are as defined in claim 1 or 2 respectively, a process for preparing an N-acylated taurine composition according to any one of claims 1 to 3.

5. An isethionic acid composition comprising a first isethionic acid compound of formula (IIIA) or a salt thereof and a second isethionic acid compound of formula (IIIB) or a salt thereof 【Chemical 4】 is Formula H ２ NR ３ and reacting with a primary amine compound to prepare a taurine composition, wherein R １ａ , R ２ａ and R ３ are as defined in claim 1 or 2 respectively. The method according to claim 4.

6. A source of bisulfite anion is of formula (IV) 【Chemical Formula 5】 (wherein R ５ is the same as R １ａ and R ２ａ defined in claim 1 or 2), further comprising the step of preparing an isethionic acid composition by reacting with an alkylene oxide), the method according to claim 5.

7. Formula (IC) ​ (wherein, R １ and R ２ are each independently selected from H or C １－４ alkyl, provided that one of R １ and R ２ is H and the other is C １－４ alkyl, R ３ is C １－６ alkyl, C ２－６ alkenyl, or C substituted with an aryl group １－６ alkyl, and R ４ is C ４－２５ alkyl or C ４－２５ alkenyl, and the C ４－２５ alkyl or C ４－２５ alkenyl may be substituted by hydroxy), an N-acylated taurine compound or a salt thereof.

8. R １ and R ２ are each independently selected from H or C １－２ alkyl (e.g., methyl), provided that one of R １ and R ２ is H and the other is C １－２ alkyl, R ３ is C １－６ alkyl (e.g., C １－２ alkyl), and R ４ is C ８－１８ alkyl or C ８－１８ alkenyl, and the C ８－１８ alkyl or C ８－１８ alkenyl may be substituted by hydroxy, the N-acylated taurine compound of formula (IC) according to claim 7.

9. The first taurine compound of formula (IIA) or a salt thereof and the second taurine compound of formula (IIB) or a salt thereof [Chemical Formula 7] (wherein R １ａ and R ２ａ is C １－４ alkyl, and R １ａ and R ２ａ are the same and R ３ is C １－６ alkyl, C ２－６ alkenyl or aryl group-substituted C １－６ alkyl), and a taurine composition containing the same.

10. R １ａ and R ２ａ is C １－２ alkyl (e.g., methyl), and R １ａ and R ２ａ are the same, and R ３ is C １－６ alkyl (e.g., C １－２ alkyl), the taurine composition according to claim 9.

11. Use of the composition according to any one of Claims 1 to 3 or the compound according to Claim 7 or 8 in the formulation of personal care, home care, industrial or agricultural products.

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