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: # imgabs 0 # and (b) a second N-acylated taurine compound of formula (IB) or a salt thereof: # imgabs 1 # wherein R1a and R2a are C1-4 alkyl groups wherein R1a and R2a are the same; r3 is a C1-6 alkyl group, a C2-6 alkenyl group or a C1-6 alkyl group substituted by an aryl group; and R4 is a C4-25 alkyl group or a C4-25 alkenyl group, wherein the C4-25 alkyl group or the C4-25 alkenyl group is optionally substituted by a hydroxyl group.

Description

Field of the Invention

[0001] The present invention relates to an N-acylated taurine composition and a method for preparing the N-acylated taurine composition. The N-acylated taurine composition comprises an isomeric mixture of N-acylated taurine compounds. The present invention also provides N-acylated taurine compounds and taurine compositions. The N-acylated taurine compositions and compounds can be used in a wide range of applications.

[0002] background

[0003] Taurate compounds (e.g., N-methyltaurate compounds) are known as anionic surfactants and are widely used as foaming agents and cleaning agents in a wide variety of applications. These applications include personal care, home care, industrial and agricultural applications. Taurate compounds also have hydrolytic stability over a wide pH range, such as a pH range of 2 to 13. This hydrolytic stability makes taurate compounds very suitable for applications that require stability over a wide pH range.

[0004] Taurate compounds are usually provided in the form of soft or hard pastes or in the form of viscous liquids, so they need to be stored in a hot room and / or heated before use. This makes the storage and / or handling of the compounds difficult and expensive, especially on a large scale.

[0005] There is therefore a need for alternative taurate-type compounds and compositions which provide the advantageous properties of known taurate compounds but which are easier to store and / or handle at ambient temperatures.

[0006] Overview

[0007] According to a first aspect of the present invention, there is provided an N-acylated taurine composition comprising:

[0008] (a) a first N-acylated taurine compound of formula (IA) or a salt thereof:

[0009]

[0010] and (b) a second N-acylated taurine compound of formula (IB) or a salt thereof

[0011]

[0012] in

[0013] R 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a same;

[0014] R 3 C1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl; and

[0015] R 4 C 4-25 Alkyl or C 4-25 Alkenyl, where C 4-25 Alkyl or C 4-25 The alkenyl group is optionally substituted with hydroxy.

[0016] According to a second aspect of the present invention, there is provided a method for preparing the N-acylated taurine composition according to the first aspect, the method comprising reacting a taurine composition comprising a first taurine compound or a salt thereof of formula (IIA) and a second taurine compound or a salt thereof of formula (IIB) with a taurine compound of formula R 4 -C(O)OH fatty acids or their reactive derivatives:

[0017]

[0018] Where R 1a , R 2a , R 3 and R 4 Each is as defined in the first aspect of the present invention, thereby obtaining an N-acylated taurine composition.

[0019] According to the third aspect of the present invention, there is provided an N-acylated taurine compound of formula (IC) or a salt thereof:

[0020]

[0021] in:

[0022] R 1 and R 2 Each independently selected from H or C 1-4 Alkyl, provided that R 1 and R 2 One of them is H, and R 1 and R 2 The other one is C 1-4 alkyl;

[0023] R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl; and

[0024] R 4 C 4-25 Alkyl or C 4-25 alkenyl, wherein the C 4-25 Alkyl or C 4-25The alkenyl group is optionally substituted with hydroxy.

[0025] According to a fourth aspect of the present invention, there is provided a taurine composition comprising a first taurine compound or a salt thereof of formula (IIA) and a second taurine compound or a salt thereof of formula (IIB):

[0026]

[0027] in

[0028] R 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a are the same; and

[0029] R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl.

[0030] Detailed Description

[0031] Unless otherwise stated, the following terms used in the specification and claims have the following meanings.

[0032] The terms "alkyl" and "alkenyl" include straight chain and branched alkyl and alkenyl groups, respectively.

[0033] As used herein, the term "aryl" refers to an organic radical derived from an aromatic hydrocarbon by removing a hydrogen, and includes any monocyclic, bicyclic or polycyclic carbon ring, each having up to 7 members, wherein at least one ring is aromatic.

[0034] As used in the specification and the appended claims, the singular forms "a," "an," and "the" include singular and plural referents unless the context clearly dictates otherwise.

[0035] In this specification, the term "comprising" or "including" means including the specified (one or more) components, but does not exclude the presence of other components. "Mainly composed of" or "essentially composed of" means including the specified components, but excluding other components except for the components added for purposes other than achieving the technical effects of the present invention. The term "consisting of" or "composed of" means including the specified components, but excluding other components.

[0036] Where appropriate, depending on the context, the use of the terms "comprising" or "including" may also be understood to include the meaning of "consisting mainly of" or "consisting essentially of", and may also be understood to include the meaning of "consisting of" or "composed of".

[0037] As used herein, unless expressly specified otherwise, all numbers expressing values, ranges, percentage quantities may be read as if preceded by the word "about", even if the term does not expressly appear.

[0038] Numerical ranges expressed by endpoints include all integers and, where appropriate, fractions within the range (e.g., 1 to 5 may include 1, 2, 3, 4 when referring to the number of elements, and 1.5, 2, 2.75, and 3.80 when referring to measurements). The expression of endpoints also includes the endpoint values ​​themselves (e.g., 1.0 to 5.0 includes 1.0 and 5.0). Any numerical range described herein is intended to include all subranges contained therein.

[0039] The optional features listed herein may be used alone or in combination with each other where appropriate, and in particular in combination as listed in the appended claims. As described herein, the optional features of each exemplary aspect of the present invention may also be applicable to any other aspect or exemplary aspect of the present invention where appropriate. In other words, the technician reading this specification should recognize that the optional features of each aspect or embodiment of the present invention are interchangeable and combinable between different aspects of the present invention.

[0040] As used herein, the term "and / or," when used in a list of two or more items, means that any one of the listed items may be used alone or in any combination of two or more of the listed items. For example, if a list is described as containing groups A, B, and / or C, the list may contain only A; only B; only C; 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.

[0041] According to a first aspect of the present invention, there is provided an N-acylated taurine composition comprising (a) a first N-acylated taurine compound of formula (IA) or a salt thereof:

[0042]

[0043] and (b) a second N-acylated taurine compound of formula (IB) or a salt thereof:

[0044]

[0045] in

[0046] R 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a same;

[0047] R 3C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl; and

[0048] R 4 C 4-25 Alkyl or C 4-25 Alkenyl, where C 4-25 Alkyl or C 4-25 The alkenyl group is optionally substituted with hydroxy.

[0049] The N-acylated taurine composition of the first aspect of the present invention is advantageously a flowable, pumpable and / or pourable liquid at ambient temperature and typically at a temperature below ambient temperature (e.g. below 10° C., such as below 5° C. or below 0° C.). The N-acylated taurine composition of the first aspect of the present invention is advantageously a flowable, pumpable and / or pourable liquid at a temperature above −10° C. and below ambient temperature. Thus, the N-acylated taurine composition of the first aspect of the present invention is easy to handle, store and formulate.

[0050] The N-acylated taurine composition of the first aspect of the present invention is generally advantageously a substantially clear or clear liquid at ambient temperature and typically at a temperature below ambient temperature (e.g., below 10° C., such as below 5° C. or below 0° C.). The N-acylated taurine composition of the first aspect of the present invention is generally advantageously a substantially clear or clear liquid at a temperature above −10° C. and below ambient temperature. Thus, the N-acylated taurine composition of the first aspect of the present invention does not discolor or cause turbidity in other compositions when used in combination.

[0051] 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, so that the N-acylated taurine composition of the first aspect of the present invention is an isomeric composition.

[0052] R in the compound of formula (IA) and (IB) or its salt 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a Same. Appropriately, R 1a and R 2a C 1-2 Alkyl, where R 1a and R 2a Preferably, R 1a and R 2a All are methyl.

[0053] R in the compound of formula (IA) and (IB) or its salt 3 C 1-6 Alkyl, C2-6 Alkenyl or aryl substituted C 1-6 Suitably, R 3 C 1-6 Alkyl or C 2-6 More suitably, R 3 C 1-6 Alkyl groups, such as C 1-2 Preferably, R 3 It is methyl.

[0054] R in the compound of formula (IA) and (IB) or its salt 4 C 4-25 Alkyl or C 4-25 alkenyl, wherein the C 4-25 Alkyl or C 4-25 The alkenyl group is optionally substituted with a hydroxyl group. Suitably, R 4 C 4-25 Alkyl groups, such as C 8-18 Alkyl, where C 4-25 Alkyl groups, such as C 8-18 alkyl, optionally substituted by hydroxy. Suitably, R 4 For unsubstituted C 4-25 Alkyl, such as unsubstituted C 8-18 alkyl.

[0055] The R 4 Can include mixed C 4-25 Alkyl or C 4-25 Examples of suitable natural sources include fatty acid mixtures obtained directly from coconut oil or palm kernel oil, or in processing steps such as hydrogenation (e.g. to reduce unsaturated C 18 compounds) or "top extraction" (i.e. distilling off a large volume of fatty acid mixture to reduce C8 and / or C 10 The fatty acid mixture obtained after the fatty acid level is ≥ 1.

[0056] Reference to salts of compounds of formula (IA) and (IB) includes any suitable salt. For example, salts of compounds of formula (IA) and (IB) may be in the form of salts (IA') and (IB') as follows:

[0057]

[0058] Where R 1a , R 2a , R 3 and R 4 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., a sodium, potassium, lithium, calcium or magnesium cation) or an ammonium or substituted ammonium cation (e.g., a dimethylammonium or tetra-n-butylammonium cation). + It is a sodium cation.

[0059] Salts of N-acylated taurine compounds are also known as taurates.

[0060] The first aspect of the present invention can provide an N-acylated taurine composition, wherein:

[0061] R 1a and R 2a C 1-2 Alkyl (eg, methyl), where R 1a and R 2a same;

[0062] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0063] R 4 C 8-18 Alkyl or C 8-18 alkenyl, wherein the C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0064] The first aspect of the present invention can provide an N-acylated taurine composition, wherein:

[0065] R 1a and R 2a All are methyl;

[0066] R 3 C 1-2 an alkyl group (e.g., a methyl group); and

[0067] R 4 C 8-18 Alkyl or C 8-18 alkenyl, wherein the C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0068] The first aspect of the present invention can provide an N-acylated taurine composition, wherein:

[0069] R 1a and R 2a C 1-2 Alkyl (eg, methyl), where R 1a and R 2a same;

[0070] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0071] R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 Alkenyl groups are unsubstituted.

[0072] The first aspect of the present invention can provide an N-acylated taurine composition, wherein:

[0073] R 1a and R 2a All are methyl;

[0074] R 3 C 1-2 an alkyl group (e.g., a methyl group); and

[0075] R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 Alkenyl groups are unsubstituted.

[0076] The N-acylated taurine composition of the first aspect of the present invention may comprise the N-acylated taurine compounds (or salts thereof) of formula (IA) and (IB) in any suitable ratio. For example, the N-acylated taurine composition may comprise a first N-acylated taurine compound or salt thereof of formula (IA) and a second N-acylated taurine compound or salt thereof of formula (IB) in a molar ratio of 99:1 to 1:99, such as 99:1 to 1:1. A preferred ratio 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.

[0077] 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, the method comprising reacting 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 with a taurine compound of formula R 4 -C(O)OH fatty acids or their reactive derivatives:

[0078]

[0079] Where R 1a , R 2a , R 3 and R 4Each is as defined herein, thereby providing an N-acylated taurine composition. 4 Any suitable reactive derivative of -C(O)OH, such as an acyl chloride R 4 -C(O)Cl.

[0080] The first taurine compound of formula (IIA) and the second taurine compound of formula (IIB) (or their salts) in the taurine composition are structural isomers, so this represents an isomer (taurine) mixture. For example, the taurine composition can contain the first taurine compound of formula (IIA) and the second taurine compound of formula (IIB) (or their salts) in a molar ratio of 99:1 to 1:99 (e.g., 99:1 to 1:1). A preferred ratio can be, for example, 99:1 to 4:1 or 9:1 to 4:1. Other preferred ratios can be 85:15 or 97:3.

[0081] Taurine composition and formula R 4 -C(O)OH fatty acid or its reactive derivative is reacted under any suitable reaction conditions, wherein R 1a , R 2a , R 3 and R 4 Each is as defined herein. The reaction can be carried out under any suitable reaction conditions, depending on the specific reagents used.

[0082] For example, when the taurine composition is combined with the formula R 4 When the fatty acid of -C(O)OH is reacted, the suitable reaction temperature is 160 to 230° C. At this time, the reaction can be carried out in the presence of a suitable catalyst. Suitable catalysts are well known to those skilled in the art.

[0083] When the taurine composition is combined with the formula R 4 -C(O)OH fatty acid derivatives, such as fatty acid chlorides R 4 When reacting -C(O)Cl, the suitable reaction temperature is 45 to 75°C, for example 50 to 65°C.

[0084] Any suitable reaction solvent may be used, such as water or alcohol, preferably water. The reaction is usually carried out at a pH of 9.5 to 10.5, which may be maintained by adding a suitable base (such as sodium hydroxide) or adding a suitable buffer.

[0085] The method of the second aspect of the present invention may also include: preparing a taurine composition by reacting an isethionic acid composition comprising a first isethionic acid compound or a salt thereof of formula (IIIA) and a second isethionic acid compound or a salt thereof of formula (IIIB) with a primary amine compound of formula H2NR3:

[0086]

[0087] Thus, a taurine composition is obtained.

[0088] References to salts of compounds of formula (IIIA) and (IIIB) include any suitable salt. For example, salts of compounds of formula (IIIA) and (IIIB) may be in the form of salts (IIIA') and (IIIB') as follows:

[0089]

[0090] Where R 1a and R 2a Each is 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., a sodium, potassium, lithium, calcium or magnesium cation) or an ammonium or substituted ammonium cation (e.g., a dimethylammonium or tetra-n-butylammonium cation). + It is a sodium cation.

[0091] Therefore, the method for preparing an N-acylated taurine composition according to the first aspect of the present invention may include:

[0092] (1) a isethionic acid composition comprising a first isethionic acid compound (IIIA) or a salt thereof and a second isethionic acid compound (IIIB) or a salt thereof is reacted with a compound of formula H2NR 3 The primary amine compounds react:

[0093]

[0094] Thus, a taurine composition comprising a first taurine compound or a salt thereof of formula (IIA) and a second taurine compound or a salt thereof of formula (IIB) is obtained:

[0095]

[0096] and (2) mixing the taurine composition obtained in step (1) with a taurine compound of formula R 4 -C(O)OH fatty acid or its reactive derivative, wherein R 1a , R 2a , R 3 and R 4 Each is as defined herein, thereby obtaining an N-acylated taurine composition.

[0097] The first isethionate compound (IIIA) and the second isethionate compound (IIIB) (or their salts) in the isethionate composition are structural isomers, and thus this represents a mixture of isomers (isethionates). A typical molar ratio of the first isethionate compound (IIIA) to the second isethionate compound (IIIB) (or their salts) in the isethionate composition may be from 99:1 to 1:1, for example from 99:1 to 4:1.

[0098] Isethionic acid compositions comprising a first isethionic acid compound (IIIA) or a salt thereof and a second isethionic acid compound (IIIB) or a salt thereof are well known and can be obtained by any suitable means, for example as described in US 8105993. Typically, the isethionic acid composition is prepared and / or provided as an isomer mixture and reacted without separating the isomers.

[0099] For example, an isethionate composition comprising a first isethionate compound (IIIA) or a salt thereof and a second isethionate compound (IIIB) or a salt thereof may be prepared by subjecting a source of bisulfite anions (e.g., a bisulphite anion of the formula HO—S(O)—O - X + ) is reacted with an alkylene oxide of formula (IV) to prepare:

[0100]

[0101] Where R 5 With R 1a and R 2a Same, and X + is a cation as defined herein (e.g. wherein m is 1). The 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, such as about 7. The reaction can be carried out at a temperature of 20 to 200° C., such as 30 to 95° C., such as 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.

[0102] The isethionic acid composition may be reacted with the primary amine under any suitable reaction conditions. A suitable reaction temperature is from 200 to 280° C., such as from 220 to 260° C. Any suitable reaction solvent may be used, such as water and / or aliphatic alcohols, preferably water.

[0103] The method of the second aspect of the invention may comprise removing excess H2NR from the reaction product 3 The step of reacting the primary amine compound, such as the isethionic acid composition with the primary amine is completed.

[0104] According to the third aspect of the present invention, there is provided an N-acylated taurine compound of formula (IC) or a salt thereof:

[0105]

[0106] in:

[0107] R 1 and R 2 Each independently selected from H or C 1-4 Alkyl, provided that R 1 and R 2 One of them is H, and R 1 and R 2 The other one is C 1-4 alkyl;

[0108] R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl; and

[0109] R 4 C 4-25 Alkyl or C 4-25 Alkenyl, where C 4-25 Alkyl or C 4-25 The alkenyl group is optionally substituted with hydroxy.

[0110] In the compound of formula (IC) or its salt, R 1 and R 2 Selected from H and C 1-4 Alkyl, provided that R 1 and R 2 One of them is H, and R 1 and R 2 The other one is C 1-4 Suitably, R 1 and R 2 One of them is C 1-4 alkyl and the other is H. Suitably, R 1 and R 2 One of them is C 1-2 alkyl and the other is H. Suitably, R 1 and R 2 One of the two is methyl and the other is H.

[0111] In one embodiment, in the compound of formula (IC) or a salt thereof, R 1 C 1-4 Alkyl and R 2 is H. Suitably, R 1 C 1-2 Alkyl and R 2 is H. Suitably, R1 is methyl and R 2 For H.

[0112] In one embodiment, in the compound of formula (IC) or a salt thereof, R 2 C 1-4 Alkyl and R 1 is H. Suitably, R 2 C 1-2 Alkyl and R 1 is H. Suitably, R 2 is methyl and R 1 For H.

[0113] In the compound of formula (IC) or its salt, R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 Suitably, R 3 C 1-6 Alkyl or C 2-6 More suitably, R 3 C 1-6 Alkyl groups, such as C 1-2 Preferably, R 3 It is methyl.

[0114] In the compound of formula (IC) or its salt, R 4 C 4-25 Alkyl or C 4-25 alkenyl, wherein the C 4-25 Alkyl or C 4-25 The alkenyl group is optionally substituted with a hydroxyl group. Suitably, R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with a hydroxyl group. Suitably, R in the compound of formula (IC) 4 For unsubstituted C 8-18 Alkyl or unsubstituted C 8-18 Alkenyl.

[0115] In the compound of formula (IC) or its salt, R 4 Can be C 4-25 Alkyl groups, such as C 8-18 Alkyl, where C 4-25 Alkyl or C 8-18 The alkyl group is optionally substituted with a hydroxyl group. Suitably, R 4 Can be unsubstituted C 4-25 Alkyl, such as unsubstituted C 8-18 alkyl

[0116] References to salts of compounds of formula (IC) include any suitable salt. For example, a salt of a compound of formula (IC) may be in the form of a salt (IC') as follows:

[0117]

[0118] Where R 1 , R 2 , R 3 and R 4 Each is 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., a sodium, potassium, lithium, calcium or magnesium cation) or an ammonium or substituted ammonium cation (e.g., a dimethylammonium or tetra-n-butylammonium cation). + It is a sodium cation.

[0119] The third aspect of the present invention can provide an N-acylated taurine compound of formula (IC) or a salt thereof, wherein:

[0120] R 1 and R 2 Each independently selected from H or C 1-2 Alkyl (e.g. methyl), provided that R 1 and R 2 One of them is H, and R 1 and R 2 The other one is C 1-2 alkyl;

[0121] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0122] R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0123] The third aspect of the present invention can provide an N-acylated taurine compound of formula (IC) or a salt thereof, wherein:

[0124] R 1 C 1-4 Alkyl and R 2 For H.

[0125] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl);

[0126] R 4 C8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0127] The third aspect of the present invention can provide an N-acylated taurine compound of formula (IC) or a salt thereof, wherein:

[0128] R 1 C 1-2 Alkyl and R 2 H

[0129] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0130] R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0131] The third aspect of the present invention can provide an N-acylated taurine compound of formula (IC) or a salt thereof, wherein:

[0132] R 1 is methyl, and R 2 H

[0133] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0134] R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0135] The third aspect of the present invention can provide an N-acylated taurine compound of formula (IC) or a salt thereof, wherein:

[0136] R 2 C 1-4 Alkyl and R 1 is H;

[0137] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0138] R 4 C 8-18Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0139] The third aspect of the present invention can provide an N-acylated taurine compound of formula (IC) or a salt thereof, wherein:

[0140] R 2 C 1-2 Alkyl and R 1 is H;

[0141] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0142] R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0143] The third aspect of the present invention can provide an N-acylated taurine compound of formula (IC) or a salt thereof, wherein:

[0144] R 2 is methyl and R 1 is H;

[0145] R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and

[0146] R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

[0147] The N-acylated taurine compound of the third aspect of the invention may be prepared by any suitable method. For example, the N-acylated taurine compound may be isolated from the N-acylated taurine composition according to the first aspect of the invention, i.e. by isolating the compound from the composition. The N-acylated taurine compound may be prepared from an appropriate taurine compound (e.g. isolated from a taurine composition as defined herein) by reaction with a fatty acid or a reactive derivative thereof as defined herein.

[0148] According to a fourth aspect of the present invention, there is provided a taurine composition comprising a first taurine compound or a salt thereof of formula (IIA) and a second taurine compound or a salt thereof of formula (IIB):

[0149]

[0150] in

[0151] R 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a are the same; and

[0152] R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl.

[0153] The first and second taurine compounds in the taurine composition of the fourth aspect of the present invention are structural isomers, and thus the taurine composition of the fourth aspect of the present invention is an isomeric (taurine) composition.

[0154] In the compounds of formula (IIA) and (IIB) (or their salts), R 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a Same. Appropriately, R 1a and R 2a C 1-2 Alkyl, where R 1a and R 2a Preferably, R 1a and R 2a All are methyl.

[0155] In the compounds of formula (IIA) and (IIB) (or their salts), R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 Suitably, R 3 C 1-6 Alkyl or C 2-6 More suitably, R 3 C 1-6 Alkyl groups, such as C 1-2 Preferably, R 3 It is methyl.

[0156] Reference to salts of compounds of formula (IIA) and (IIB) includes any suitable salt.

[0157] For example, under basic conditions, the salts of compounds of formula (IIA) and (IIB) may be in the form of the following sulfonates (IIA') and (IIB') (wherein the amine group is in its free base form):

[0158]

[0159] Where R 1a , R 2a and R 3 Each is 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., a sodium, potassium, lithium, calcium or magnesium cation) or an ammonium or substituted ammonium cation (e.g., a dimethylammonium or tetra-n-butylammonium cation). + It is a sodium cation.

[0160] For example, under acidic conditions, the salts of the compounds of formula (IIA) and (IIB) may be in the form of the following ammonium salts (IIA") and (IIB") (wherein the sulfonic acid group is in its free acid form):

[0161]

[0162] Where R 1a , R 2a and R 3 Each is as defined herein.

[0163] For example, at the isoelectric point, the salts of the compounds of formula (IIA) and (IIB) may be in the form of zwitterions (also called inner salts or internal salts). For example, the salts of the compounds of formula (IIA) and (IIB) may be in the form of the following zwitterions (IIA'') and (IIIB''):

[0164]

[0165] Where R 1a , R 2a and R 3 Each is as defined herein.

[0166] A fourth aspect of the present invention may provide a taurine composition, wherein:

[0167] R 1a and R 2a C 1-2 Alkyl (eg, methyl), where R 1a and R 2a are the same; and

[0168] R 3 C 1-6 Alkyl (e.g. C 1-2alkyl).

[0169] A fourth aspect of the present invention may provide a taurine composition, wherein:

[0170] R 1a and R 2a are methyl; and

[0171] R 3 C 1-2 Alkyl (eg, methyl).

[0172] The taurine composition of the fourth aspect of the present invention may comprise taurine compounds (or salts thereof) of formula (IIA) and (IIB) in any suitable ratio. For example, the taurine composition may comprise a first taurine compound or salt thereof of formula (IIA) and a second taurine compound or salt thereof of formula (IIB) in a molar ratio of 99:1 to 1:99 (e.g., 99:1 to 1:1). A preferred ratio 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.

[0173] The taurine composition of the fourth aspect of the present invention can be prepared by any suitable method, for example, by reacting an isethionate salt composition comprising a first isethionate compound of formula (IIIA) and a second isethionate compound of formula (IIIB) (or a salt thereof) with a taurine salt of formula H2NR 3 The primary amine compound is reacted as described herein in relation to the second aspect of the invention.

[0174] The composition of the first aspect of the invention and the compound of the third aspect of the invention can be used in a variety of applications. The present invention also provides the use of the composition according to the first aspect of the invention or the compound according to the third aspect of the invention in formulating personal care, home care, industrial or agricultural products. BRIEF DESCRIPTION OF THE DRAWINGS

[0176] For a better understanding of the invention, and to show exemplary embodiments of how the invention may be carried into effect, reference will now be made, by way of example only, to the accompanying drawings, in which:

[0177] Figure 1 shows the physical form of the Sodium Cocoyl N-methyl Methyl Taurate composition of Example 2 at ambient temperature and at a concentration of 30.4 wt % active matter in water; and

[0178] Figure 2 The physical form of Sodium Cocoyl N-methyltaurate of Example 3 is shown at ambient temperature and at concentrations of 30 to 31.5 wt % active matter in water.

[0179] The invention will now be further described with reference to the following non-limiting examples. Example

[0180] Example 1 (Present Invention) - Synthesis of N-Methyl Methyltaurine Isomer Mixture

[0181] A 1 L stainless steel autoclave was equipped with an overhead stirrer, thermocouple, pressure gauge and bursting disk. 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 maintained at this temperature for 5.5 hours. A pressure increase to about 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 removing excess methylamine, the vacuum was gradually increased to 125 mbar at a bath temperature of 70° C. to partially remove water. The active substance content of the partially concentrated product was 60 wt %.

[0182] The reaction product sample was concentrated to dryness. 1 H and 13 C NMR analysis (D2O) showed that the sodium N-methyl methyl taurate product (mixture of isomers) was the major component. The molar ratio of the isomers was calculated based on NMR integration to be 97:3 (sodium 2-(methylammonium) propane-1-sulfonate:sodium 1-(methylammonium) propane-2-sulfonate).

[0183] Example 2 (Present Invention) - Synthesis of a Mixture of Isomers of Sodium Cocoyl N-Methyl Methyl Taurate

[0184] A 1 L jacketed reactor was equipped with an overhead stirrer, thermometer, pH probe, and dropping funnel. N-methyl methyl taurate (60 wt % solution, 121.6 g, 0.416 mol) and water (238 g) were charged. Agitation was initiated and the reaction mass was heated to 55° C. Cocoyl chloride (94.75 g, 0.43 mol) was charged via the dropping funnel over 3 hours; while the reaction pH was maintained in the range of 9.5-10.5 by manual addition of 50 wt % aqueous NaOH solution (about 37 g total). After the addition of cocoyl chloride was complete, the reaction temperature was raised to 65° C. and maintained for 1 hour. The reaction mass was cooled to 50° C. and the pH was 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 %.

[0185] Example 3 (Comparative) - Sodium Cocoyl N-Methyl Taurate

[0186] Sodium cocoyl-N-methyl taurate (trade name: WS Conc) sample. This material was prepared from N-methyltaurine in a manner similar to Example 2 and had an active substance content of 30-31.5% by weight.

[0187] Example 4 - Comparison of Physical Forms of Sodium Cocoyl N-Methyl Taurate Isomer Mixture and Sodium Cocoyl N-Methyl Taurate

[0188] The physical forms of the sodium cocoyl N-methyl taurate isomer mixture (Example 2) and sodium cocoyl N-methyl taurate (Example 3) at the same active substance concentration were compared at ambient temperature.

[0189] The results are shown in Table 1.

[0190] Table 1 Comparison of physical forms of sodium cocoyl N-methyl taurate isomer mixture and sodium cocoyl N-methyl taurate

[0191]

[0192]

[0193] * Commercial product specifications

[0194] These results demonstrate the surprising advantages of the product of the invention. Since it is liquid at room temperature, storage and handling are greatly improved, and no preheating is required for transfer operations.

[0195] Figure 1 (Example 2, invention) and 2 (Example 3, comparative) show the products at ambient temperature.

[0196] Example 5 - Physical Form of Sodium Cocoyl N-Methyl Methyl Taurate Isomer Mixture at Reduced Temperature

[0197] The experiment was designed to simulate storage conditions in a refrigerated warehouse.

[0198] A sample (100 g) of the product of Example 2 was cooled in steps. For each cooling step, the product was kept at the temperature for 30 minutes and the physical morphology of the product was visually inspected. The results are shown in Table 2.

[0199] Table 2 Physical form of Example 2 at reduced temperature

[0200] Temperature(℃) Physical form 5℃ Clear, thin liquid 0℃ Clear, thin liquid -5℃ Clarify liquid and make it more viscous -10℃ Some solids appear -15℃ Sample solidification

[0201] This experiment shows that the product of the invention of Example 2 remains completely liquid at temperatures as low as -5° C. This has significant advantages in commercial use, as the material can be stored in non-temperature controlled warehouses for most climates.

[0202] The cooled Example 2 sample was then allowed to warm to ambient temperature. At a temperature of -8°C, the sample quickly became completely liquid again.

[0203] The present invention is not limited to the details of the foregoing (one or more) embodiments. The present invention covers any novel feature or any novel combination of features disclosed in this specification (including any accompanying claims, abstract and drawings), or any novel step or any novel combination of steps in any disclosed method or process.

Claims

1. 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: in R 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a same; R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl; and R 4 C 4-25 Alkyl or C 4-25 Alkenyl, where C 4-25 Alkyl or C 4-25 The alkenyl group is optionally substituted with hydroxy.

2. The N-acylated taurine composition according to claim 1, wherein: R 1a and R 2a C 1-2 Alkyl (eg, methyl), where R 1a and R 2a same; R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

3. The N-acylated taurine composition according to claim 1 or 2, comprising a first N-acylated taurine compound or a salt thereof of formula (IA) and a second N-acylated taurine compound or a salt thereof of formula (IB) in a molar ratio of 99:1 to 1:99, such as 99:1 to 1:1, such as 99:1 to 4:

1.

4. A method for preparing an N-acylated taurine composition according to any one of claims 1 to 3, the method comprising reacting a taurine composition comprising a first taurine compound or a salt thereof of formula (IIA) and a second taurine compound or a salt thereof of formula (IIB) with a taurine compound of formula R 4 -C(O)OH fatty acids or their reactive derivatives: Where R 1a , R 2a , R 3 and R 4 As defined in claim 1 or 2 respectively, thereby providing an N-acylated taurine composition.

5. The method according to claim 4, further comprising reacting 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 with a isethionic acid compound of formula H2NR 3 The taurine composition is prepared by reacting a primary amine compound: Where R 1a , R 2a and R 3 As defined in claim 1 or 2 respectively, thereby providing a taurine composition.

6. The method of claim 5, further comprising preparing the isethionic acid composition by reacting a source of bisulfite anions with an alkylene oxide of formula (IV): Where R 5 R as defined in claim 1 or 2 1a and R 2a same.

7. An N-acylated taurine compound of formula (IC) or a salt thereof: in: R 1 and R 2 Each independently selected from H or C 1-4 Alkyl, provided that R 1 and R 2 One of them is H, and R 1 and R 2 The other one is C 1-4 alkyl; R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl; and R 4 C 4-25 Alkyl or C 4-25 Alkenyl, where C 4-25 Alkyl or C 4-25 The alkenyl group is optionally substituted with hydroxy.

8. The N-acylated taurine compound of formula (IC) according to claim 7, wherein: R 1 and R 2 Each independently selected from H or C 1-2 Alkyl (e.g. methyl), provided that R 1 and R 2 One of them is H, and R 1 and R 2 The other one is C 1-2 alkyl; R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl); and R 4 C 8-18 Alkyl or C 8-18 Alkenyl, where C 8-18 Alkyl or C 8-18 The alkenyl group is optionally substituted with hydroxy.

9. A taurine composition comprising a first taurine compound or a salt thereof of formula (IIA) and a second taurine compound or a salt thereof of formula (IIB): in R 1a and R 2a C 1-4 Alkyl, where R 1a and R 2a are the same; and R 3 C 1-6 Alkyl, C 2-6 Alkenyl or aryl substituted C 1-6 alkyl.

10. The taurine composition according to claim 9, wherein: R 1a and R 2a C 1-2 Alkyl (eg, methyl), where R 1a and R 2a are the same; and R 3 C 1-6 Alkyl (e.g. C 1-2 alkyl).

11. Use of a composition according to any one of claims 1 to 3 or a compound according to claim 7 or 8 in formulating a personal care, home care, industrial or agricultural product.

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