POLYMERIC AMPHOTERIC SURFACTANT COMPOUND

Abstract

Disclosed herein is a polymeric amphoteric surfactant compound of formula (I).

Claims

1. A polymeric amphoteric surfactant compound having chemical formula I: ##STR00016## wherein: R.sub.1 represents a C.sub.8 to C.sub.22 alkyl group, a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group, a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group; o and p each independently represent a number from 2 to 8; q, q′, r and r′ each independently represent a number from 1 to 5; L.sub.1 to L.sub.3 each independently represent a C.sub.1 to C.sub.3 alkyl group; R.sub.2 and R.sub.3 each independently represent a C.sub.1 to C.sub.3 alkyl group; R.sub.4 represents OH or a C.sub.1 to C.sub.3 alkyl group; R.sub.5 to R.sub.8 each independently represent a C.sub.8 to C.sub.22 alkyl group; 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 R.sub.1 represents a C.sub.8 to C.sub.16 alkyl group.

3. The polymeric amphoteric surfactant compound according to claim 2, wherein R.sub.1 represents a C.sub.8, C.sub.10, C.sub.12, C.sub.14 or C.sub.16 alkyl group.

4. The polymeric amphoteric surfactant compound according to claim 1, wherein R.sub.1 represents a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group, a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group.

5. The polymeric amphoteric surfactant compound according to claim 4, wherein: o and p each independently represent a number from 3 to 5; and q, q′, r and r′ each independently represent a number from 1 to 3.

6. The polymeric amphoteric surfactant compound according to claim 4, wherein R.sub.1 represents a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group or a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group.

7. The polymeric amphoteric surfactant compound according to claim 1, wherein R.sub.2 and R.sub.3 are methyl.

8. The polymeric amphoteric surfactant compound according to claim 1, wherein: R.sub.4 represents OH; and/or R.sub.5 to R.sub.8 each independently represent a C.sub.8 to C.sub.16 alkyl group.

9. The polymeric amphoteric surfactant compound according to claim 1, wherein: L.sub.1 represents CH.sub.2; and/or L.sub.2 represents (CH.sub.2).sub.3; and/or L.sub.3 represents CH.sub.2.

10. A polymeric amphoteric surfactant formulation comprising one or more compounds of formula I as defined in claim 1, wherein: (a) when R.sub.1 is a C.sub.8 to C.sub.22 alkyl group, then the formulation is formed of compounds of formula I having the same R.sub.1 group or is formed from a mixture of compounds of formula I having different R.sub.1 groups; (b) when R.sub.1 is a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group, a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group, then the formulation is formed of compounds of formula I having the same R.sub.1 group.

11. A composition comprising: a polymeric amphoteric surfactant compound according to claim 1.

12. A method of forming a compound according to formula I, the method comprising the step of reacting a compound for formula II: ##STR00017## with a compound of formula III: ##STR00018## in the presence of a suitable solvent and a suitable base, wherein: L.sub.1 to L.sub.3, R.sub.1 to R.sub.4, n and m are as defined in claim 1; X is a leaving group; and Y.sup.+ is a monovalent metal cation.

13. The method according to claim 12, wherein the compound of formula II is formed by reaction of a compound of formula IV: ##STR00019## with a compound of formula V: ##STR00020## in the presence of a suitable solvent and a suitable base, wherein: R.sub.1 represents a C.sub.8 to C.sub.22 alkyl group, a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group, a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group; o and p each independently represent a number from 2 to 8; q, q′, r and r′ each independently represent a number from 1 to 5; L.sub.1 and L.sub.2 each independently represent a C.sub.1 to C.sub.3 alkyl group; R.sub.2 and R.sub.3 each independently represent a C.sub.1 to C.sub.3 alkyl group; 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; and R.sub.9 represents H or C.sub.1 to C.sub.3 alkyl.

14. The method according to claim 13, wherein the compound of formula IV is formed by reaction of a compound of formula VI: ##STR00021## with a compound of formula VII: ##STR00022## in the presence of a suitable solvent and a suitable base, wherein: R.sub.1 represents a C.sub.8 to C.sub.22 alkyl group, a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group, a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group; o and p each independently represent a number from 2 to 8; q, q′, r and r′ each independently represent a number from 1 to 5; 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; R.sub.9 represents H or C.sub.1 to C.sub.3 alkyl; X′ represents a leaving group; and L.sub.1′ represents a bond or a C.sub.1 to C.sub.2 alkyl group.

15. The polymeric amphoteric surfactant compound according to claim 1, wherein R.sub.1 represents a C.sub.8 to C.sub.14 alkyl group.

16. The polymeric amphoteric surfactant compound according to claim 1, wherein R.sub.1 represents a C.sub.8 to C.sub.12 alkyl group or a C.sub.12 to C.sub.14 alkyl group.

17. The polymeric amphoteric surfactant compound according to claim 3, wherein R.sub.1 represents a C.sub.8, C.sub.10 or C.sub.12 alkyl group.

18. The method according to claim 12, wherein one or both of the following apply: X is selected from Cl, Br or I; and Y.sup.+is Na.sup.+.

19. The method according to claim 14, wherein X′ represents Cl, Br or I.

20. A composition comprising: a polymeric amphoteric surfactant formulation according to claim 10.

Description

BRIEF DESCRIPTION OF DRAWINGS

[0032] FIG. 1 depicts a schematic representation of the current invention to prepare intermediate 20 by subjecting an alkyl polyglycoside (10) to a two-step amination reaction.

[0033] FIG. 2 depicts a schematic representation of the current invention to prepare compound 30 by subjecting intermediate 20 to a sulfonation reaction.

DESCRIPTION

[0034] The current invention relates to novel polymeric amphoteric surfactant compounds. The current invention particularly relates to sultaines derived from carbohydrate-based surfactants. These compounds have a very mild odour and do not add colour to formulations they are added to. Moreover, they produce dense foams with high stability when used in combination with other surfactants, and demonstrate excellent stability in both extreme acidic and alkaline conditions. These properties make them suitable for diverse applications such as personal care (e.g. skin care and deodorants), household and industrial products, and enhanced oil recovery. It is believed that they can replace conventional amphoteric surfactants such as betaines, amphoacetates and amphopropionates.

[0035] Thus in a first aspect of the invention, there is provided a polymeric amphoteric surfactant compound having chemical formula I:

##STR00008##

wherein: [0036] R.sub.1 represents a C.sub.8 to C.sub.22 alkyl group, a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group [0037] a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group; [0038] and p each independently represent a number from 2 to 8; [0039] q, q′, r and r′ each independently represent a number from 1 to 5; [0040] L.sub.1 to L.sub.3 each independently represent a C.sub.1 to C.sub.3 alkyl group; [0041] R.sub.2 and R.sub.3 each independently represent a C.sub.1 to C.sub.3 alkyl group; [0042] R.sub.4 represents OH or a C.sub.1 to C.sub.3 alkyl group; [0043] R.sub.5 to R.sub.8 each independently represent a C.sub.8 to C.sub.21 alkyl group; [0044] 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.

[0045] In embodiments herein, the word “comprising” may be interpreted as requiring the features mentioned, but not limiting the presence of other features. Alternatively, the word “comprising” may also relate to the situation where only the components/features listed are intended to be present (e.g. the word “comprising” may be replaced by the phrases “consists of” or “consists essentially of”). It is explicitly contemplated that both the broader and narrower interpretations can be applied to all aspects and embodiments of the present invention. In other words, the word “comprising” and synonyms thereof may be replaced by the phrase “consisting of” or the phrase “consists essentially of” or synonyms thereof and vice versa.

[0046] Unless otherwise stated, the term “alkyl” refers to an unbranched or branched, cyclic, saturated or unsaturated (so forming, for example, an alkenyl or alkynyl) hydrocarbyl radical, which may be substituted or unsubstituted (with, for example, one or more halo atoms).

[0047] It will be appreciated that in embodiments of the invention, the alkyl group may have an acyclic part and a cyclic part. When the alkyl group contains a cyclic portion group (which may be where the group “cycloalkyl” is specified), then the cyclic portion is preferably C.sub.3-12 cycloalkyl and, more preferably, C.sub.5-10 (e.g. C.sub.5-7) cycloalkyl. In said embodiments, the remaining acrylic portion may be C.sub.1-22 linear or C.sub.4-22 branched acyclic alkyl that is saturated or unsaturated.

[0048] Unless otherwise specified herein, where the term “alkyl” refers to an acyclic group, it is preferably C.sub.1-22 alkyl.

[0049] As noted herein before, R.sub.1 may be an alkyl group (i.e. a C.sub.8 to C.sub.22 alkyl group) or an alkoxy group (i.e. a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group). When R.sub.1 is a C.sub.8 to C.sub.22 alkyl group, the term alkyl may be construed broadly to cover the definitions provided hereinbefore. However, in particular embodiments of the invention that may be mentioned herein, the C.sub.8 to C.sub.22 alkyl group may refer to a linear or branched, saturated or unsaturated hydrocarbyl group. In yet more particular embodiments of the invention, the C.sub.8 to C.sub.22 alkyl group may refer to a branched or, yet more particularly, a linear saturated hydrocarbyl group.

[0050] Any possible degree of branching is contemplated and said branched alkyl groups may be obtained from any suitable method. For example, suitable branched alkyl chains may be obtained by use of the Guerbet Reaction between two primary alkyl alcohols. Examples of suitable branched alkyl alcohols that may be used to provide the R.sub.1 groups mentioned herein following 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.

[0051] In embodiments of the invention that may be mentioned herein, when R.sub.1 is an alkyl group, it may be a C.sub.8 to C.sub.16 alkyl group, such as a C.sub.8 to C.sub.14 alkyl group, such as a C.sub.8 to C.sub.12 alkyl group or a C.sub.12 to C.sub.14 alkyl group. For example, R.sub.1 may represent a C.sub.8, C.sub.10, C.sub.12, C.sub.14 or C.sub.16 alkyl group, such as a C.sub.8, C.sub.10 or C.sub.12 alkyl group. Again, these groups may be branched or, more particularly, linear alkyl groups.

[0052] In embodiments of the invention where R.sub.1 is an alkoxy group, it may be a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group. For example, R.sub.1 may represent a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group or a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group.

[0053] As mentioned above, o and p may each independently represent a number from 2 to 8. For example, o and p may each independently represent a number from 3 to 5. As mentioned above, q, q′, r and r′ may each independently represent a number from 1 to 5, for example, q, q′, r and r′ may each independently represent a number from 1 to 3.

[0054] Any suitable C.sub.1-C.sub.3 alkyl group may be R.sub.2 and R.sub.3 (e.g. methyl, ethyl, propyl and isopropyl). However, in particular embodiments of the invention that may be mentioned herein, R.sub.2 and R.sub.3 may both be a methyl group.

[0055] As noted above, R.sub.4 may represent OH. In addition or independently, R.sub.5 to R.sub.8 may each independently represent a C.sub.8 to C.sub.16 alkyl group.

[0056] The L groups mentioned hereinbefore (L.sub.1 to L.sub.3) may each represent a suitable linking group selected from a C.sub.1 to C.sub.3 alkyl group (CnH.sub.2n-2). Examples of suitable linking groups include CH.sub.2, (CH.sub.2).sub.2 and (CH.sub.2).sub.3. In particular embodiments of the invention that may be mentioned herein: [0057] L.sub.1 may represent CH.sub.2; and/or [0058] L.sub.2 may represent (CH.sub.2).sub.3; and/or [0059] L.sub.3 may represent CH.sub.2.

[0060] In particular embodiments of the invention, n may be 1 and m may be 0.

[0061] In a particular embodiment of the invention, the compound of formula I is:

##STR00009##

wherein: [0062] R.sub.1 represents a C.sub.12 or C.sub.14 alkyl group; and [0063] n represents a number from 1 to 5 and m represents a number from 0 to 4, where the sum of [0064] n+m is from 1 to 5, provided that n is at least 1.

[0065] It will be appreciated that the above-mentioned embodiments may be combined in any suitable combination that is technically sensible.

[0066] As will be appreciated, one or more of the polymeric amphoteric surfactants of formula I may be combined together to provide a polymeric amphoteric surfactant formulation. This may be particularly the case where R.sub.1 is selected from an alkyl group, as a mixture of different alkyl groups may be used to provide compounds of formula I. In which case a mixture of different compounds of formula I are provided as the reaction product (discussed in more detail below in the examples). Thus, in another aspect of the invention, there is provided a polymeric amphoteric surfactant formulation comprising one or more compounds of formula I as defined above such that: [0067] (i) when R.sub.1 is a C.sub.8 to C.sub.22 alkyl group, then the formulation is formed of compounds of formula I having the same R.sub.1 group or is formed from a mixture of compounds of formula I having different R.sub.1 groups; and [0068] (j) when R.sub.1 is a —((CH.sub.2).sub.2O).sub.o—R.sub.5 group, a —((CH(CH.sub.3)CH.sub.2).sub.pO)—R.sub.6 group a —((CH.sub.2).sub.2O).sub.q—((CH(CH.sub.3)CH.sub.2).sub.rO)—R.sub.7 group, or a —((CH(CH.sub.3)CH.sub.2).sub.q′O)—((CH.sub.2).sub.2O).sub.r′—R.sub.8 group, then the formulation is formed of compounds of formula I having the same R.sub.1 group.

[0069] The above is intended to refer to the reaction products obtained from the reactions conducted below. As will be appreciated, the compounds of formula I can be mixed together after formation in any suitable ratio should that be desired to produce additional formulations.

[0070] In a further aspect of the 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 may be a foaming composition for use in oil recovery operations, a household or industry cleaning composition, or a composition for use in personal care (for example, a hair shampoo composition or deodorant composition).

[0071] The composition for use in oil recovery operations may comprise from 5 to 90% by weight of the polymeric amphoteric surfactant compound of chemical formula I as defined above; or a polymeric amphoteric surfactant formulation as defined above.

[0072] The household or industry cleaning composition may comprise from 5 to 50% by weight of the polymeric amphoteric surfactant compound of chemical formula I as defined above; or a polymeric amphoteric surfactant formulation as defined above.

[0073] The composition for use in personal care may comprise from 5 to 30% by weight of the polymeric amphoteric surfactant compound of chemical formula I as defined above; or a polymeric amphoteric surfactant formulation as defined above.

[0074] A further aspect of the invention relates to the formation of the compounds of formula I disclosed hereinbefore. Thus, there is also disclosed a method of forming a compound according to formula I, the method comprising the step of reacting a compound for formula II:

##STR00010##

with a compound of formula III:

##STR00011##

in the presence of a suitable solvent and a suitable base, wherein: [0075] L.sub.1 to L.sub.3, R.sub.1 to R.sub.4, n and m are as defined above; [0076] X is a leaving group (e.g. Cl, Br or I); and [0077] Y.sup.+ is a monovalent metal cation (e.g. Na.sup.+).

[0078] In such embodiments, the method may be conducted such that the compound of formula II is formed by reaction of a compound of formula IV:

##STR00012##

with a compound of formula V:

##STR00013##

in the presence of a suitable solvent and a suitable base, wherein: [0079] L.sub.1, L.sub.2, R.sub.1 to R.sub.3, n and m are as defined above; and [0080] R.sub.9 represents H or C.sub.1 to C.sub.3 alkyl.

[0081] In further embodiments, the method may be conducted such that the wherein the compound of formula IV is formed by reaction of a compound of formula VI:

##STR00014##

with a compound of formula VII:

##STR00015##

in the presence of a suitable solvent and a suitable base, wherein: [0082] R.sub.1, n and m are as defined above; [0083] R.sub.9 represents H or C.sub.1 to C.sub.3 alkyl; [0084] X′ represents a leaving group (e.g. Cl, Br or I); and [0085] L.sub.1′ represents a bond or a C.sub.1 to C.sub.2 alkyl group.

[0086] In particular embodiments of the invention, the compound of formula VI is FM600/FM1200 (CAS: 110615-47-9). The degree of polymerisation of the compound is from 1.4 to 1.6, and m and n may be defined accordingly.

[0087] Further aspects and embodiments of the invention are provided in the following non-limiting examples.

EXAMPLES

Materials and Methods

[0088] The materials were purchased from the sources as provided below.

[0089] Alkyl polyglycoside (APG)—two specific APGs from Fenchem Biotek were used. [0090] i. FM600/FM1200—solid content: 50 wt % in water (CAS: 110615-47-9) with the following composition: [0091] C10:<1.0%; [0092] C12:70-76%; [0093] C14: 24-30%; and [0094] C16: <1.0%. [0095] ii. FM425N (CAS: 68515-73-1 & 110615-47-9) with the following composition: [0096] C8: 29-35%; [0097] C10: 25-32%; [0098] C12: 27-33%; [0099] C14: 7-13%; and [0100] C16: 1.0% max

[0101] Sodium methoxide (Sigma-Aldrich, CAS 124-41-4, 95% purity, powder)

[0102] Ethyl chloroacetate (Sigma-Aldrich, CAS 105-39-5, 99% purity)

[0103] 3-(dimethylamino)-1-propylamine (Sigma-Aldrich, CAS-109-55-7, 98% purity)

[0104] 3-chloro-2-hydroxypropanesulfonic acid sodium salt (Sigma-Aldrich or Alfa Aesar, PubChem

[0105] Substance ID 329786196, 98% purity)

[0106] .sup.1H NMR was recorded on a Bruker 400 MHz Spectrometer.

[0107] All reactions were performed under nitrogen atmosphere unless expressly stated.

[0108] When provided, conversion values are the percentage of the amount of target products and byproducts (if any) over the amount of starting material. Yield values are the percentage of the amount of target products only over the amount of starting material.

[0109] Chloride content was analysed to determine reaction completion and was conducted in accordance to APHA Method 4500-CI; method validation was performed to confirm that it is suitable for surfactant sample matrix.

[0110] Free amine content was analysed to determine reaction completion and was conducted in accordance to ASTM 2074; method validation is in-progress to confirm that it is suitable for surfactant sample matrix.

Example 1

[0111] Compound 30 was synthesized according to the schematic representations of FIG. 1 and FIG. 2. An alkyl polyglycoside 10 is first subjected to a two-step amination reaction to give a tertiary-amine intermediate 20. The intermediate 20 is then subjected to a sulfonation reaction to give an alkyl polyglycoside-based sultaine 30.

Synthesis and Characterisation of 15

[0112] Typically, an alkyl polyglycoside (FM600/FM1200; 10; 50 g, 0.1297 mol) and water (50 ml) were introduced to a 4-neck round bottom flask equipped with an agitator, thermometer, a water-cooled condenser and a sparger 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 (about 97% yield). The reaction was monitored by chloride content analysis and stopped when the theoretical chloride content is reached. The resulting product 15 was characterised by .sup.1H NMR. .sup.1H NMR (400 MHz, Methanol-d.sub.4) 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).

[0113] The formation of 15 was confirmed by the presence of peaks at the 4.1 to 4.4 ppm region in the .sup.1H NMR spectrum, which correspond to the hydrogens present in the moiety 14 that is incorporated in the glycoside.

Synthesis and Characterisation of 20

[0114] Typically, 3-(dimethylamino)-1-propylamine (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. While sodium methoxide 12 is a reactant/catalyst for forming 20, there is no further addition of sodium methoxide 12 in this step (i.e. 12 present in the reaction solution with 15 comes from the first step). The reaction mixture was then heated to about 85° C. to 90° C. and maintained for about 4 to 6 hours to form a solution of 20 (>80% yield and >90% conversion). The reaction was monitored by free amine analysis and stopped when the free amine value is less than about 0.5 wt %. The resulting product 20 was characterised by .sup.1H NMR. .sup.1H NMR (400 MHz, Methanol-d.sub.4) 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).

[0115] The formation of 20 was confirmed by the presence of a peak at 8.56 ppm, corresponding to the tertiary amine group.

Synthesis and Characterisation of 30

[0116] Typically, 3-chloro-2-hydroxypropanesulfonic acid sodium salt (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 is about 93-95%). The reaction was monitored by chloride content analysis and stopped when the theoretical chloride content is reached. The resulting product 30 was characterised by .sup.1H NMR. .sup.1H NMR (400 MHz, Methanol-d.sub.4) 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).

[0117] The formation of 30 was confirmed by chemical shifts corresponding to the two methyl groups (—CH.sub.3) attached to the nitrogen atom in the 2.92 to 3.06 ppm, and a downfield peak at 3.2 ppm corresponding to the CH.sub.2 next to the nitrogen atom having two methyl groups.

Comparative Example 1

[0118] Compound 20 was synthesized from 10 by the procedure of Example 1 except ethyl choloroacetate (14) was replaced with chloroacetic acid. However, this results in an exothermic reaction with reduced yield (>80% conversion and >74% yield).

[0119] Without wishing to be bound by theory, it is believed that the use of ethyl choloroacetate (14) promotes site-selective amination at the C6 position of the alkyl polyglycoside and reduces the formation of byproducts and mixtures.

Comparative Example 2

[0120] Instead of a 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 yield and conversion (>75% conversion and >70% yield). In addition this reaction is not economically viable as 3-dimethylamino-1-propyl chloride hydrochloride is an expensive reactant.

Comparative Example 3

[0121] 3-(dimethylamino)-1-propylamine (16) can be replaced by chloroamine. However, the use of chloroamine is not economically viable due to its cost.

Example 2

[0122] Performance evaluation is being carried out for the surfactants (including 20). They include foaming, mildness test (Zein test), viscosity thickening, surface tension & CMC and wetting.