Polymeric amphoteric surfactant compound

Abstract

Disclosed herein are polymeric amphoteric surfactant compounds of formula (I).

Description

Technical Field

[0001] The present invention relates to polymeric amphoteric surfactant compounds, particularly those derived from carbohydrates. Background Art

[0002] The listing or discussion of previously published documents in this specification should not necessarily be taken as an admission that such documents are part of the prior art or common general knowledge.

[0003] Carbohydrate-based surfactants are environmentally friendly and biodegradable surfactants developed from carbohydrates and vegetable oils. Alkyl polyglycosides (APGs) are specific non-ionic carbohydrate-based surfactants prepared from glucose and fatty alcohols. However, currently available carbohydrate-based surfactants do not necessarily exhibit good performance in terms of foaming, viscosity thickening, surface tension (or critical micelle concentration), wetting, and / or water solubility. Since they typically produce poor-quality foam, especially in the presence of oil and hard water, they may not be suitable for enhanced oil recovery applications. In addition, they are known to have a higher irritation potential in personal care applications.

[0004] Amphoteric surfactants can be derived from carbohydrate-based surfactants. Sultaines and betaines are two such examples. Generally, sultaines are superior to betaines because they have a lower skin irritation potential. However, there is still a need for improved surfactant compositions that address one or more of the above problems. Summary of the Invention

[0005] Aspects and embodiments of the present invention are described in the following items.

[0006] 1. A polymeric amphoteric surfactant compound having the chemical formula I:

[0007]

[0008] Wherein:

[0009] R1 represents C8 to C 22 alkyl, –((CH2)2O) o -R5 group, –((CH(CH3)CH2) p O)-R6 group, –((CH2)2O) q -((CH(CH3)CH2) r O)-R7 group, or -((CH(CH3)CH2) q’ O)-((CH2)2O) r’ -R8 group;

[0010] o and p each independently represent a number from 2 to 8;

[0011] q, q’, r and r’ each independently represent a number from 1 to 5;

[0012] L1 to L3 each independently represent a C1 to C3 alkyl group;

[0013] R2 and R3 each independently represent a C1 to C3 alkyl group;

[0014] R4 represents OH or a C1 to C3 alkyl group;

[0015] R5 to R8 each independently represent a C8 to C 22 alkyl group;

[0016] n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of n + m is from 1 to 5, provided that n is at least 1.

[0017] 2. The polymeric amphoteric surfactant compound according to item 1, wherein R1 represents a C8 to C 16 alkyl group. For example, a C8 to C 14 alkyl group, such as a C8 to C 12 alkyl group or a C 12 to C 14 alkyl group.

[0018] 3. The polymeric amphoteric surfactant compound according to item 2, wherein R1 represents a C8, C 10 , C 12 , C 14 or C 16 alkyl group, optionally, wherein R1 represents a C8, C 10 or C 12 alkyl group.

[0019] 4. The polymeric amphoteric surfactant compound according to item 1, wherein R1 represents a –((CH2)2O) o -R5 group, a –((CH(CH3)CH2) p O)-R6 group, a –((CH2)2O) q -((CH(CH3)CH2) r O)-R7 group, or a -((CH(CH3)CH2) q’ O)-((CH2)2O) r’ -R8 group.

[0020] 5. The polymeric amphoteric surfactant compound according to item 4, wherein:

[0021] o and p each independently represent a number from 3 to 5; and

[0022] q, q', r, and r' each independently represent a number from 1 to 3.

[0023] 6. The polymeric amphoteric surfactant compound according to item 4 or 5, wherein R1 represents –((CH2)2O) o -R5 group or –((CH(CH3)CH2) p O)-R6 group.

[0024] 7. The polymeric amphoteric surfactant compound according to any one of the preceding items, wherein R2 and R3 are methyl.

[0025] 8. The polymeric amphoteric surfactant compound according to any one of the preceding items, wherein:

[0026] R4 represents OH; and / or

[0027] R5 to R8 each independently represent C8 to C 16 alkyl.

[0028] 9. The polymeric amphoteric surfactant compound according to any one of the preceding items, wherein:

[0029] L1 represents CH2; and / or

[0030] L2 represents (CH2)3; and / or

[0031] L3 represents CH2.

[0032] 10. A polymeric amphoteric surfactant preparation comprising one or more compounds of formula I as defined in any one of items 1 to 9, wherein:

[0033] (a) When R1 is C8 to C 22 alkyl, the preparation is formed of compounds of formula I having the same R1 group or a mixture of compounds of formula I having different R1 groups;

[0034] (b) When R1 is –((CH2)2O) o -R5 group, –((CH(CH3)CH2) p O)-R6 group, –((CH2)2O) q -((CH(CH3)CH2) r O)-R7 group, or -((CH(CH3)CH2) q’ O)-((CH2)2O) r’ -R8 group, the preparation is formed of compounds of formula I having the same R1 group.

[0035] 11. A composition comprising:

[0036] A polymeric amphoteric surfactant compound according to any one of items 1 to 9; or

[0037] A polymeric amphoteric surfactant preparation according to item 10.

[0038] 12. A method for forming a compound according to Formula I, the method comprising the step of reacting a compound of Formula II with a compound of Formula III in the presence of a suitable solvent and a suitable base:

[0039]

[0040] Wherein:

[0041] L1 to L3, R1 to R4, n and m are as defined in any one of items 1 to 9;

[0042] X is a leaving group (e.g., Cl, Br or I); and

[0043] Y + is a monovalent metal cation (e.g., Na + ).

[0044] 13. The method according to item 12, wherein the compound of Formula II is formed by reacting a compound of Formula IV with a compound of Formula V in the presence of a suitable solvent and a suitable base:

[0045]

[0046]

[0047] Wherein:

[0048] L1, L2, R1 to R3, n and m are as defined in any one of items 1 to 9; and

[0049] R9 represents H or C1 to C3 alkyl.

[0050] 14. The method according to item 13, wherein the compound of Formula IV is formed by reacting a compound of Formula VI with a compound of Formula VII in the presence of a suitable solvent and a suitable base:

[0051]

[0052] Wherein:

[0053] R1, n and m are as defined in any one of items 1 to 9;

[0054] R9 represents H or C1 to C3 alkyl;

[0055] X’ represents a leaving group (e.g., Cl, Br or I); and

[0056] L 1’ represents a bond or a C1 to C2 alkyl group. BRIEF DESCRIPTION OF THE DRAWINGS

[0057] Figure 1 A schematic diagram depicting the preparation of intermediate 20 by subjecting alkyl polyglycoside (10) to a two-step amination reaction according to the present invention.

[0058] Figure 2 A schematic diagram depicting the preparation of compound 30 by subjecting intermediate 20 to a sulfonation reaction according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0059] The present invention relates to novel polymeric amphoteric surfactant compounds. The present invention particularly relates to sulfobetaines derived from carbohydrate-based surfactants. These compounds have a very mild odor and do not add color to the formulations to which they are added. In addition, when used in combination with other surfactants, they produce a dense foam with high stability and exhibit excellent stability under both extreme acidic and alkaline conditions. These properties make them suitable for a variety of applications such as personal care (e.g., skin care and deodorant), household products, and industrial products, as well as enhanced oil recovery. It is believed that they can replace conventional amphoteric surfactants such as betaines, amphoacetates, and amphopropionates.

[0060] Thus, in a first aspect of the present invention, there is provided a polymeric amphoteric surfactant compound having the chemical formula I:

[0061]

[0062] wherein:

[0063] R1 represents a C8 to C 22 alkyl group, –((CH2)2O) o -R5 group, –((CH(CH3)CH2) p O)-R6 group, –((CH2)2O) q -((CH(CH3)CH2) r O)-R7 group, or -((CH(CH3)CH2) q’ O)-((CH2)2O) r’ -R8 group;

[0064] o and p each independently represent a number from 2 to 8;

[0065] q, q’, r, and r’ each independently represent a number from 1 to 5;

[0066] L1 to L3 each independently represent a C1 to C3 alkyl group;

[0067] Each of R2 and R3 independently represents a C1-C3 alkyl group;

[0068] R4 represents OH or a C1-C3 alkyl group;

[0069] Each of R5 to R8 independently represents a C8-C 22 alkyl group;

[0070] n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of n + m is from 1 to 5, provided that n is at least 1.

[0071] In the embodiments herein, the term "comprising" can be interpreted as requiring the recited features, but not precluding the presence of other features. Optionally, the term "comprising" can also relate to the case where only the recited components / features are intended to be present (e.g., the term "comprising" can be replaced by the phrase "consisting of" or "consisting essentially of"). It is expressly contemplated that both the broader and narrower interpretations can be applied to all aspects and embodiments of the present invention. In other words, the term "comprising" and its synonyms can be replaced by the phrase "consisting of" or the phrase "consisting essentially of" or their synonyms, and vice versa.

[0072] Unless otherwise specified, the term "alkyl" refers to a straight-chain or branched-chain, cyclic, saturated or unsaturated (thus forming, for example, an alkenyl or alkynyl group) hydrocarbon group, which may be substituted or unsubstituted (by, for example, one or more halogen atoms).

[0073] It will be understood that in the embodiments of the present invention, an alkyl group can have an acyclic portion and a cyclic portion. When the alkyl group contains a cyclic moiety group (which may be the case defined as the group "cycloalkyl"), the cyclic moiety is preferably a C 3-12 cycloalkyl group, and more preferably a C 5-10 (e.g., C 5-7 ) cycloalkyl group. In said embodiments, the remaining acyclic portion can be a saturated or unsaturated C 1-22 straight-chain or C 4-22 branched-chain acyclic alkyl group.

[0074] Unless otherwise specified herein, the term "alkyl" refers to an acyclic group, which is preferably a C 1-22 alkyl group.

[0075] As previously mentioned, R1 can be an alkyl group (i.e., a C8-C 22 alkyl group) or an alkoxy group (i.e., –((CH2)2O) o -R5 group, –((CH(CH3)CH2) p O)-R6 group, –((CH2)2O) q -((CH(CH3)CH2)r an O)-R7 group, or -((CH(CH3)CH2) q’ O)-((CH2)2O) r’ -R8 group). When R1 is a C8 to C 22 alkyl group, the term alkyl group can be interpreted broadly to cover the definitions provided above. However, in specific embodiments of the invention that may be mentioned herein, the C8 to C 22 alkyl group can refer to a straight-chain or branched-chain, saturated or unsaturated hydrocarbon group. In more specific embodiments of the invention, the C8 to C 22 alkyl group can refer to a branched-chain saturated hydrocarbon group, or more particularly, a straight-chain saturated hydrocarbon group.

[0076] Any possible degree of branching is contemplated, and the branched-chain alkyl groups can be obtained by any suitable method. For example, a suitable branched-chain alkyl chain can be obtained by utilizing the Guerbet reaction between two primary alkyl alcohols. Examples of suitable branched-chain alkyl alcohols that can be used to provide the R1 groups mentioned herein according to the reaction pathways discussed below include, but are not limited to: 2-methyl-1-pentanol, 2-ethyl-1-hexanol, 2-propyl-1-heptanol, 2-butyl-1-octanol, 2-pentyl-1-nonanol, 2-hexyl-1-decanol, 2-heptyl-1-undecanol, 2-octyl-1-dodecanol, 2-nonyl-1-tridecanol, 2-decyl-1-tetradecanol, 2-undecyl-1-pentadecanol, 2-dodecyl-1-hexadecanol, 2-tridecyl-1-heptadecanol, 2-tetradecyl-1-octadecanol, 2-pentadecyl-1-nonadecanol, 2-hexadecyl-1-eicosanol, 2-heptadecyl-1-heneicosanol, 2-octadecyl-1-docosanol, 2-nonadecyl-1-tricosanol, and 2-eicosyl-1-tetracosanol.

[0077] In embodiments of the invention that may be mentioned herein, when R1 is an alkyl group, it can be a C8 to C 16 alkyl group, such as a C8 to C 14 alkyl group, such as a C8 to C 12 alkyl group or a C 12 to C 14 alkyl group. For example, R1 can represent a C8, C 10 , C 12 , C 14 or C 16 alkyl group, such as a C8, C 10 or C 12 alkyl group. Similarly, these groups can be branched-chain alkyl groups, or more particularly, straight-chain alkyl groups.

[0078] In embodiments of the invention in which R1 is an alkoxy group, it can be –((CH2)2O)o - the R5 group, –((CH(CH3)CH2) p O)- the R6 group, –((CH2)2O) q -((CH(CH3)CH2) r O)- the R7 group, or -((CH(CH3)CH2) q’ O)-((CH2)2O) r’ - the R8 group. For example, R1 can represent –((CH2)2O) o - the R5 group or –((CH(CH3)CH2) p O)- the R6 group.

[0079] As described above, o and p can each independently represent a number from 2 to 8. For example, o and p can each independently represent a number from 3 to 5. As described above, q, q’, r and r’ can each independently represent a number from 1 to 5. For example, q, q’, r and r’ can each independently represent a number from 1 to 3.

[0080] Any suitable C1-C3 alkyl can be R2 and R3 (e.g., methyl, ethyl, propyl, and isopropyl). However, in certain embodiments of the invention that may be mentioned herein, R2 and R3 can both be methyl.

[0081] As described above, R4 can represent OH. Additionally or independently, R5 to R8 can each independently represent a C8 to C 16 alkyl.

[0082] The L groups (L1 to L3) mentioned above can each represent a suitable linking group selected from C1 to C3 alkyl (C n H 2n-2 ). Examples of suitable linking groups include CH2, (CH2)2, and (CH2)3. In certain embodiments of the invention that may be mentioned herein:

[0083] L1 can represent CH2; and / or

[0084] L2 can represent (CH2)3; and / or

[0085] L3 can represent CH2.

[0086] In certain embodiments of the invention, n can be 1 and m can be 0.

[0087] In certain embodiments of the invention, the compound of formula I is:

[0088]

[0089] Wherein:

[0090] R1 represents C 12 or C 14 alkyl; and

[0091] n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of n + m is from 1 to 5, provided that n is at least 1.

[0092] It will be understood that the above embodiments can be combined in any suitable combination that is technically reasonable.

[0093] As will be understood, one or more polymeric amphoteric surfactants of formula I can be combined together to provide a polymeric amphoteric surfactant formulation. This may be particularly the case when R1 is selected from alkyl, since mixtures of different alkyls can be used to provide compounds of formula I. In such cases, a mixture of different compounds of formula I is provided as the reaction product (discussed in more detail below in the Examples). Thus, in another aspect of the present invention, there is provided a polymeric amphoteric surfactant formulation comprising one or more compounds of formula I as defined above, such that:

[0094] (i) when R1 is C8 to C 22 alkyl, then the formulation is formed from compounds of formula I having the same R1 group or from a mixture of compounds of formula I having different R1 groups; and

[0095] (j) when R1 is –((CH2)2O) o -R5 group, –((CH(CH3)CH2) p O)-R6 group, –((CH2)2O) q -((CH(CH3)CH2) r O)-R7 group, or -((CH(CH3)CH2) q’ O)-((CH2)2O) r’ -R8 group, then the formulation is formed from compounds of formula I having the same R1 group.

[0096] The above is intended to mean the reaction product obtained from the reaction carried out below. As will be understood, the compounds of formula I can be mixed together in any suitable ratio after formation, which ratio should be required for the production of other formulations.

[0097] In another aspect of the present invention, there is provided a composition comprising a polymeric amphoteric surfactant compound of chemical formula I as defined above or a polymeric amphoteric surfactant formulation as defined above. Such compositions can be foaming compositions for oil recovery operations, household cleaning compositions or industrial cleaning compositions, or compositions for personal care (e.g., shampoo compositions or deodorant compositions).

[0098] The composition for oil recovery operations may comprise from 5% to 90% by weight of the polymeric amphoteric surfactant compound of formula I as defined above or the polymeric amphoteric surfactant preparation as defined above.

[0099] The household cleaning composition or the industrial cleaning composition may comprise from 5% to 50% by weight of the polymeric amphoteric surfactant compound of formula I as defined above or the polymeric amphoteric surfactant preparation as defined above.

[0100] The composition for personal care may comprise from 5% to 30% by weight of the polymeric amphoteric surfactant compound of formula I as defined above or the polymeric amphoteric surfactant preparation as defined above.

[0101] Another aspect of the present invention relates to the formation of the compound of formula I disclosed above. Accordingly, a method for forming a compound according to formula I is also disclosed, which method comprises the step of reacting a compound of formula II with a compound of formula III in the presence of a suitable solvent and a suitable base:

[0102]

[0103]

[0104] Wherein:

[0105] L1 to L3, R1 to R4, n and m are as defined above;

[0106] X is a leaving group (e.g., Cl, Br or I); and

[0107] Y + is a monovalent metal cation (e.g., Na + ).

[0108] In such embodiments, the method may be carried out such that the compound of formula II is formed by the reaction of a compound of formula IV with a compound of formula V in the presence of a suitable solvent and a suitable base:

[0109]

[0110] Wherein:

[0111] L1, L2, R1 to R3, n and m are as defined above; and

[0112] R9 represents H or C1 to C3 alkyl.

[0113] In a further embodiment, the method may be carried out such that the compound of formula IV is formed by the reaction of a compound of formula VI with a compound of formula VII in the presence of a suitable solvent and a suitable base:

[0114]

[0115] Wherein:

[0116] R1, n, and m are as defined above;

[0117] R9 represents H or C1-C3 alkyl;

[0118] X’ represents a leaving group (e.g., Cl, Br, or I); and

[0119] L 1’ represents a bond or C1-C2 alkyl.

[0120] In a particular embodiment of the present invention, the compound of formula VI is FM600 / FM1200 (CAS: 110615-47-9). The degree of polymerization of the compound is 1.4 to 1.6, and m and n can be defined accordingly.

[0121] Other aspects and embodiments of the present invention are provided in the following non-limiting examples.

[0122] Examples

[0123] Materials and Methods

[0124] Materials were purchased from the sources provided below.

[0125] Alkyl polyglycoside (APG) - Two specific APGs from Fenchem Biotek were used.

[0126] i. FM600 / FM1200 - Solid content: 50 wt% in water (CAS: 110615-47-9), having the following composition:

[0127] C10: <1.0%;

[0128] C12: 70 - 76%;

[0129] C14: 24 - 30%; and

[0130] C16: <1.0%.

[0131] ii. FM425N (CAS: 68515-73-1 & 110615-47-9), having the following composition:

[0132] C8: 29 - 35%;

[0133] C10: 25 - 32%;

[0134] C12: 27 - 33%;

[0135] C14: 7 - 13%; and

[0136] C16: up to 1.0%

[0137] Sodium methoxide (Sigma - Aldrich, CAS 124 - 41 - 4, purity 95%, powder)

[0138] Ethyl chloroacetate (Sigma - Aldrich, CAS 105 - 39 - 5, purity 99%)

[0139] 3 - (Dimethylamino)-1 - propylamine (Sigma - Aldrich, CAS - 109 - 55 - 7, purity 98%)

[0140] Sodium 3 - chloro - 2 - hydroxypropanesulfonate (Sigma - Aldrich or Alfa Aesar, PubChem Substance ID 329786196, purity 98%)

[0141] Recorded on a Bruker 400MHz spectrometer 1 H NMR.

[0142] Unless otherwise specified, all reactions were carried out under a nitrogen atmosphere.

[0143] When provided, the conversion value is the percentage of the amounts of the target product and by - products (if any) relative to the amount of the starting materials. The yield value is the percentage of the amount of only the target product relative to the amount of the starting materials.

[0144] The chloride content was analyzed to determine the completion of the reaction and was carried out according to APHA method 4500 - Cl; method validation was carried out to confirm its suitability for the surfactant sample matrix.

[0145] The free amine content was analyzed to determine the completion of the reaction and was carried out according to ASTM 2074; method validation is in progress to confirm its suitability for the surfactant sample matrix.

[0146] Example 1

[0147] According to Figure 1 and Figure 2 the schematic diagram of, compound 30 was synthesized. First, the alkyl polyglycoside 10 was subjected to a two - step amination reaction to obtain the tertiary amine intermediate 20. Then, the intermediate 20 was subjected to a sulfonation reaction to obtain the alkyl polyglycoside - based sulfobetaine 30.

[0148] Synthesis and characterization of 15

[0149] Typically, alkyl polyglycoside (FM600 / FM1200; 10; 50 g, 0.1297 mol) and water (50 ml) were introduced into a four-necked round-bottom flask equipped with a stirrer, thermometer, water-cooled condenser, and a nebulizer for introducing nitrogen. Sodium methoxide (12; 6.8 g, 0.1261 mol) and ethyl chloroacetate (14; 15.5 g, 0.1261 mol) were added to the flask, and the resulting mixture was heated to about 85 °C to 90 °C and maintained for about 4 to 6 hours to form a reaction solution containing 15 (yield about 97%). The reaction was monitored by chloride content analysis and stopped when the theoretical chloride content was reached. The resulting product 15 was characterized by 1 1H NMR. 1 1H NMR (400 MHz, methanol-d4) δ 4.79 (d, J = 3.8 Hz, 1H), 4.35–4.15 (m, 1H), 4.00–3.10 (m, 11H), 1.70–1.06 (m, 26H), 1.06–0.75 (m, 3H).

[0150] The formation of 15 was confirmed by the presence of a peak in the 4.1 ppm to 4.4 ppm region in the 1 1H NMR spectrum, which corresponds to the hydrogen present in the moiety 14 where the glycoside was introduced.

[0151] Synthesis and characterization of 20

[0152] Typically, 3-(dimethylamino)-1-propanamine (16; 12.2 g, 0.1198 mol) was added to the reaction solution containing 15 (about 55 g, 0.1261 mol) from the first step. Although sodium methoxide 12 is a reactant / catalyst for forming 20, no further sodium methoxide 12 was added in this step (i.e., the 12 present in the reaction solution containing 15 was from the first step). Then the reaction mixture was heated to about 85 °C to 90 °C and maintained for about 4 to 6 hours to form a solution of 20 (yield > 80% and conversion > 90%). The reaction was monitored by free amine analysis and stopped when the free amine value was less than about 0.5 wt%. The resulting product 20 was characterized by 1 1H NMR. 1 1H NMR (400 MHz, methanol-d4) δ 8.56 (s, 1H), 4.79 (d, J = 3.8 Hz, 1H), 4.27 (d, J = 7.8 Hz, 1H), 4.00–3.11 (m, 14H), 2.45–2.35 (m, 4H), 2.27 (s, 12H), 1.71 (p, J = 7.3 Hz, 4H), 1.31 (d, J = 5.5 Hz, 24H), 0.96–0.87 (m, 3H).

[0153] The formation of 20 was confirmed by the presence of a peak at 8.56 ppm, which corresponds to the tertiary amine group.

[0154] Synthesis and Characterization of 30

[0155] Typically, sodium 3-chloro-2-hydroxypropanesulfonate (18; 24.64 g, 0.1198 mol) was added to the reaction solution containing 20 from the second step. The reaction mixture was then heated to about 85 °C to 90 °C and maintained for about 5 to 7 hours to form a solution of 30 (yield of about 93 - 95%). The reaction was monitored by chloride content analysis and stopped when the theoretical chloride content was reached. The resulting product 30 was characterized by 1 1H NMR. 1 1H NMR (400 MHz, methanol-d4) δ 8.56 (s, 1H), 4.83–4.75 (m, 1H), 4.39–4.17 (m, 1H), 4.00–3.13 (m, 15H), 3.09–2.55 (m, 7H), 1.86–1.75 (m, 2H), 1.70–1.57 (m, 2H), 1.31 (d, J = 5.1 Hz, 17H), 0.95–0.87 (m, 3H).

[0156] The formation of 30 was confirmed by the chemical shift corresponding to two methyl groups (-CH3) attached to the nitrogen atom at 2.92 ppm to 3.06 ppm and a downfield peak at 3.2 ppm corresponding to CH2 adjacent to the nitrogen atom with two methyl groups.

[0157] Comparative Example 1

[0158] Compound 20 was synthesized from 10 by the procedure of Example 1 except that ethyl chloroacetate (14) was replaced with chloroacetic acid. However, this led to an exothermic reaction with a reduced yield (conversion > 80% and yield > 74%).

[0159] Without wishing to be bound by theory, it is believed that the use of ethyl chloroacetate (14) promotes site-selective amination at the C6 position of alkyl polyglycosides and reduces the formation of by-products and mixtures.

[0160] Comparative Example 2

[0161] Instead of the two-step amination reaction outlined in Example 1, a one-step amination reaction can be achieved by reacting 10 with 3-dimethylamino-1-propyl chloride hydrochloride. This also results in reduced yields and conversions (conversion > 75% and yield > 70%). In addition, this reaction is not economically viable because 3-dimethylamino-1-propyl chloride hydrochloride is an expensive reactant.

[0162] Comparative Example 3

[0163] 3-(Dimethylamino)-1-propanamine (16) can be replaced by chloramine. However, due to the cost of chloramine, the use of chloramine is not economically feasible.

[0164] Example 2

[0165] The performance of surfactants (including 20) is being evaluated. They include foaming, mildness test (zein test), viscosity thickening, surface tension, and CMC and wetting.

Claims

1. A polymeric amphoteric surfactant compound having the chemical formula I: Wherein: R1 represents C8 to C 16 alkyl; L1 to L3 each independently represent a C1 to C3 alkyl group; R2 and R3 each independently represent a C1 to C3 alkyl group; R4 represents OH; n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of n + m is from 1 to 5, provided that n is at least 1.

2. The polymeric amphoteric surfactant compound according to claim 1, wherein R1 represents C8, C 10 , C 12 , C 14 or C 16 alkyl.

3. The polymeric amphoteric surfactant compound according to claim 2, wherein R1 represents C8, C 10 or C 12 alkyl.

4. The polymeric amphoteric surfactant compound according to claim 1, wherein R2 and R3 are methyl groups.

5. The polymeric amphoteric surfactant compound according to claim 1, wherein: L1 represents CH2; and / or L2 represents (CH2)3; and / or L3 represents CH2.

6. The polymeric amphoteric surfactant compound according to any one of the preceding claims, wherein the polymeric amphoteric surfactant compound is:

7. A polymeric amphoteric surfactant preparation comprising one or more compounds of formula I as defined in claim 1, wherein: When R1 is C8 to C 16 alkyl, the preparation is formed from a compound of formula I having the same R1 group or from a mixture of compounds of formula I having different R1 groups.

8. A composition comprising: The polymeric amphoteric surfactant compound according to claim 1; or The polymeric amphoteric surfactant preparation according to claim 7.

9. A method for forming a compound of formula I according to claim 1, the method comprising the step of reacting a compound of formula II with a compound of formula III in the presence of a suitable solvent and a suitable base: Wherein: L1 to L3, R1 to R4, n and m are as defined in claim 1; X is a leaving group; and Y + is a monovalent metal cation.

10. The method according to claim 9, wherein X is Cl, Br or I.

11. The method according to claim 9, wherein Y + is Na + .

12. The method according to any one of claims 9 to 11, wherein the compound of formula II is formed by the reaction of a compound of formula IV with a compound of formula V in the presence of a suitable solvent and a suitable base: Wherein: L1, L2, R1 to R3, n and m are as defined in claim 1; and R9 represents H or a C1 to C3 alkyl group.

13. The method according to claim 12, wherein the compound of formula IV is formed by the reaction of a compound of formula VI with a compound of formula VII in the presence of a suitable solvent and a suitable base: Wherein: R1, n and m are as defined in any one of claims 1 to 6; R9 represents H or a C1 to C3 alkyl group; X’ is a leaving group; and L 1’ represents a bond or a C1 to C2 alkyl group.

14. The method according to claim 13, wherein X’ represents Cl, Br or I.

Images