Polymeric amphoteric surfactant compounds

Abstract

The present disclosure is a polymeric amphoteric surfactant compound of formula (I):

Description

[Technical Field]

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

[0002] background The listing or discussion of a prior-published document in this specification should not necessarily be taken as an acknowledgement that the document is part of the state of the art or is general knowledge.

[0003] Carbohydrate surfactants are environmentally friendly, biodegradable surfactants developed from carbohydrates and vegetable oils. Alkyl polyglycosides (APGs) are specific nonionic carbohydrate surfactants prepared from glucose and fatty alcohols. However, currently available carbohydrate surfactants do not always exhibit good performance in terms of foaming, viscosity thickening, surface tension (or critical micelle concentration), wetting, and / or water solubility. They generally produce poor-quality foam and may not be suitable for enhanced oil recovery applications, especially in the presence of oil and hard water. Furthermore, they are known to be highly irritating in personal care applications.

[0004] Amphoteric surfactants can be derived from carbohydrate surfactants. Sultaines and betaines are two such examples. Generally, sultaines are preferred over betaines because they have a lower skin irritation potential. However, there remains a need for improved surfactant compositions that address one or more of the above problems (or one or more, or one or more than one, or more than one) Summary of the Invention [Means for solving the problem]

[0005] Summary of the Invention Aspects and embodiments of the present invention are described in the following sections. Item 1 Chemical formula I: [ka] [In the above chemical formula I, R1 is C8~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’ represents an -R8 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; L1 to L3 each independently represent a C1 to C3 alkyl group; R2 and R3 each independently represent a C1-C3 alkyl group; R4 represents OH or a C1-C3 alkyl group; R5 to R8 are each independently C8 to C 22 represents an 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 and n is at least 1. A polymeric amphoteric surfactant compound having the formula: Section 2 R1 is C8~C 14 C8-C, such as alkyl groups 12 Alkyl groups such as or C 12 ~C 14 C8-C alkyl groups 16 Item 2. The polymeric amphoteric surfactant compound according to Item 1, wherein the amphoteric surfactant compound represents an alkyl group. Section 3 R1, C8, C 10 , C 12 , C 14 or C 16 represents an alkyl group, and optionally R1 is C8, C 10 or C 12 Item 3. The polymeric amphoteric surfactant compound according to Item 2, wherein the amphoteric surfactant compound represents an alkyl group. Section 4 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’ Item 2. The polymeric amphoteric surfactant compound according to item 1, wherein the polymeric amphoteric surfactant compound represents an —R8 group. Section 5 o and p each independently represent a number from 3 to 5; Item 5. The polymeric amphoteric surfactant compound according to Item 4, wherein q, q', r, and r' each independently represent a number of 1 to 3. Section 6 R1 is -((CH2)2O) o -R5 group or -((CH(CH3)CH2) p Item 6. The polymeric amphoteric surfactant compound according to item 4 or 5, wherein R represents an O)—R group. Section 7 Item 10. The polymeric amphoteric surfactant compound according to any one of the preceding items, wherein R2 and R3 are methyl. Section 8 R4 represents OH, and / or R5 to R8 are each independently C8 to C 16 10. The polymeric amphoteric surfactant compound according to any one of the preceding items, wherein the group represents an alkyl group. Section 9 L1 represents CH2, and / or L2 represents (CH2)3, and / or 3. The polymeric amphoteric surfactant compound according to any one of the preceding items, wherein L3 represents CH2. Section 10 (a) R1 is C8~C 22 When R is an alkyl group, the blend may be formed from compounds of formula I having the same R group, or from a mixture of compounds of formula I having different R groups; (b) 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’ A polymeric amphoteric surfactant formulation comprising one or more compounds of formula I as defined in any one of paragraphs 1 to 9, wherein when -R8 group is represented, the formulation is formed from compounds of formula I having the same R1 group. Section 11 Item 10. The polymeric amphoteric surfactant compound according to any one of Items 1 to 9, or Item 11. A composition comprising the polymeric amphoteric surfactant blend according to item 10. Section 12 1. A method of forming a compound according to formula I, comprising: The process comprises reacting a compound of formula II: [ka] of formula III: [ka] [In the above formula II and formula III, L1 to L3, R1 to R4, n and m are as defined in any one of items 1 to 9. X is a leaving group (e.g., Cl, Br, or I); Y + is a monovalent metal cation (e.g., Na + ) is] with a compound of formula (I). Section 13 The compound of formula II can be converted to a compound of formula IV: [ka] Compounds of formula V: [ka] [In the above formula IV and formula V, L1, L2, R1-R3, n, and m are as defined in any one of items 1-9; R9 represents H or C1-C3 alkyl. Item 13. The method of claim 12, wherein the compound is formed by reacting the compound with a compound of formula (I). Section 14 The compound of formula IV can be converted to a compound of formula VI: [ka] Compounds of formula VII: [ka] [In the above formula VI and formula VII, R1, n, and m are as defined in any one of clauses 1-9; R9 represents H or C1-C3 alkyl; X' represents a leaving group (e.g., Cl, Br, or I); L 1’ represents a bond or a C1-C2 alkyl group. Item 14. The method of claim 13, wherein the compound is formed by reacting the compound with a compound of formula (I). [Brief explanation of the drawings]

[0006] BRIEF DESCRIPTION OF THE DRAWINGS [Figure 1] FIG. 1 shows a schematic diagram of the present invention for preparing intermediate 20 by subjecting alkyl polyglycoside (10) to a two-step amination reaction. [Figure 2] FIG. 2 shows a schematic diagram of the present invention for preparing compound 30 by subjecting intermediate 20 to a sulfonation reaction. DETAILED DESCRIPTION OF THE INVENTION

[0007] explanation The present invention relates to novel polymeric amphoteric surfactant compounds. In particular, the invention relates to sultaines derived from carbohydrate-based surfactants. These compounds have a very mild odor and do not add color to formulations to which they are added. Furthermore, when used in combination with other surfactants, they produce highly stable, dense foam 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 deodorants), household and industrial products, and enhanced oil recovery. They are believed to be capable of replacing traditional amphoteric surfactants such as betaines, amphoacetates, and amphopropionates.

[0008] Thus, in a first aspect of the present invention, a compound of formula I: [ka] [In the above chemical formula I, R1 is C8~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’ represents an -R8 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; L1 to L3 each independently represent a C1 to C3 alkyl group; R2 and R3 each independently represent a C1-C3 alkyl group; R4 represents OH or a C1-C3 alkyl group; R5 to R8 are each independently C8 to C 22 represents an 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 and n is at least 1. There is provided a polymeric amphoteric surfactant compound having the formula:

[0009] In embodiments herein, the word "comprising" may be interpreted as requiring the recited features, but not limiting the presence of other features. Alternatively, the word "comprising" may also relate to a situation in which only the listed elements (or components) / features are intended to be present (e.g., the word "comprising" may be replaced with the phrase "consists of" or "consists essentially of"). It is expressly intended that both broader and narrower interpretations are applicable to all aspects and embodiments of the present invention. In other words, the term "comprising" and its synonyms may be replaced with the phrase "consisting of" or "consist essentially of" or their synonyms, and vice versa.

[0010] Unless otherwise specified, the term "alkyl" refers to an unbranched or branched, cyclic, saturated or unsaturated (so formed, e.g., alkenyl or alkynyl) hydrocarbon radical, which may be substituted or unsubstituted (e.g., by one or more halo atoms).

[0011] In embodiments of the present invention, it is understood that alkyl groups can have acyclic and cyclic moieties. When an alkyl group includes a cyclic moiety (the group "cycloalkyl" may be specified), the cyclic moiety is preferably C 3~12 cycloalkyl, more preferably C 5~10 (For example, C 5~7 ) cycloalkyl. In said embodiment, the remaining acyclic moiety is a saturated or unsaturated C 1~22 Linear or C 4~22 It may be a branched acyclic alkyl.

[0012] Unless otherwise stated herein, when the term "alkyl" refers to an acyclic group, it is preferably a C 1~22 It is alkyl.

[0013] As mentioned above, R1 is an alkyl group (i.e., C8 to C 22 alkyl group) or alkoxy group (i.e., -((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), R1 may be C8 to C 22 However, in certain embodiments of the present invention that may be mentioned herein, when the alkyl group is a C8-C 22 Alkyl groups may refer to straight or branched chain, saturated or unsaturated hydrocarbyl groups. In more particular embodiments of the present invention, C8 to C 22 The alkyl group may refer to a branched, or even more specifically, a straight-chain saturated hydrocarbyl group.

[0014] Any possible degree of branching is contemplated, and the branched alkyl group can be obtained by any suitable method. For example, a suitable branched alkyl chain can be obtained by using the Guerbet reaction between two primary alkyl alcohols. Examples of suitable branched alkyl alcohols that can be used to provide the R group referred to 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, Examples include 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.

[0015] In the embodiments of the present invention that may be mentioned herein, when R1 is an alkyl group, it is a C8-C 14 C8-C, such as alkyl groups 12 Alkyl groups such as or C 12 ~C 14 C8-C alkyl groups 16 For example, R1 can be a C8, C 10 or C 12 Alkyl groups such as C8, C 10 , C 12 , C 14 or C 16 It may represent alkyl groups. Again, these groups may be branched or, more particularly, straight-chain alkyl groups.

[0016] In embodiments of the invention where R1 is an alkoxy group, it is represented by the group -((CH2)2O)o-R5, -((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’ For example, R1 may be -((CH2)2O) o -R5 group or -((CH(CH3)CH2) p O)-R6 group.

[0017] 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.

[0018] Any suitable C1-C3 alkyl group 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 groups.

[0019] As above, R4 may represent OH. Additionally or independently, R5 to R8 may each independently represent C8 to C 16 may represent an alkyl group of the formula:

[0020] The L groups (L1 to L3) previously mentioned in this specification are each a C1 to C3 alkyl group (C n H 2n-2 ) may represent a suitable linking group selected from. Examples of suitable linking groups include CH, (CH) and (CH). In certain embodiments of the invention that may be mentioned herein, L1 may represent CH2, and / or L2 may represent (CH2)3, and / or L3 may represent CH2.

[0021] In certain embodiments of the present invention, n may be 1 and m may be 0.

[0022] In certain embodiments of the invention, the compound of formula I is [ka] [In the above formula I, R1 is C 12 or C 14 represents an alkyl group represented by the formula: 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 and n is at least 1. is. It will be appreciated that the above-described embodiments may be combined in any suitable combination that is technically reasonable.

[0023] As can be understood, one or more polymeric amphoteric surfactants of formula I can be combined together to provide a polymeric amphoteric surfactant blend.This is particularly true when R1 is selected from an alkyl group, because a mixture of different alkyl groups can be used to provide a compound of formula I.In this case, a mixture of different compounds of formula I is provided as a reaction product (discussed in more detail in the following examples).Therefore, in another aspect of the present invention, there is provided a polymeric amphoteric surfactant blend comprising one or more compounds of formula I as defined above: (i) R1 is C8~C 22 When R is an alkyl group, the blend is formed from compounds of formula I having the same R group or from a mixture of compounds of formula I having different R groups; and (j) R1 is -((CH2)2O) o When it is an -R group, it is -((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’When it is a -R8 group, the blend is formed from compounds of formula I having the same R1 group.

[0024] The above is intended to refer to the reaction product obtained from the reaction carried out below. As will be appreciated, the compounds of formula I may be mixed together in any suitable ratio after production to produce additional formulations.

[0025] In a further aspect of the present invention, there is provided a composition comprising a polymeric amphoteric surfactant compound of formula I as defined above, or a polymeric amphoteric surfactant formulation as defined above. Such a composition may be a foaming composition for use in oil recovery operations, a household or industrial cleaning composition, or a composition for use in personal care (e.g., a hair shampoo composition or a deodorant composition).

[0026] Compositions for use in oil recovery operations may comprise 5 to 90% by weight of a polymeric amphoteric surfactant compound of formula I as defined above or a polymeric amphoteric surfactant blend as defined above.

[0027] The household or industrial cleaning composition may comprise 5 to 50% by weight of a polymeric amphoteric surfactant compound of formula I as defined above or a polymeric amphoteric surfactant blend as defined above.

[0028] Compositions for use in personal care may comprise 5 to 30% by weight of a polymeric amphoteric surfactant compound of formula I as defined above or a polymeric amphoteric surfactant blend as defined above.

[0029] A further aspect of the present invention relates to the formation of compounds of formula I, as disclosed above. Accordingly, a method of forming compounds according to formula I is also disclosed, which comprises reacting a compound of formula II: [ka] of formula III: [ka] [In the above formula II and formula III, L1 to L3, R1 to R4, n, and m are as defined above. X is a leaving group (e.g., Cl, Br, or I); Y + is a monovalent metal cation (e.g., Na + ) is] with a compound of formula (I).

[0030] In such embodiments, the method comprises reacting a compound of formula II with a compound of formula IV: [ka] and a compound of formula V: [ka] [In the above formula IV and formula V, L1, L2, R1 to R3, n, and m are as defined above; R9 represents H or C1-C3 alkyl. The compound may be formed by reaction with a compound of formula (I).

[0031] In a further embodiment, the method comprises reacting a compound of formula IV with a compound of formula VI: [ka] Compound VII: [ka] [In the above formula VI and formula VII, R1, n and m are as defined above; R9 represents H or C1-C3 alkyl; X' represents a leaving group (e.g., Cl, Br, or I); L 1’ represents a bond or a C1-C2 alkyl group. The compound may be formed by reaction with a compound of formula (I).

[0032] In a particular embodiment of the present invention, the compound of formula VI is FM600 / FM1200 (CAS: 110615-47-9), and the degree of polymerization of the compound is 1.4-1.6, and m and n can be defined accordingly. [Example]

[0033] Further aspects and embodiments of the present invention are provided in the following non-limiting examples.

[0034] Example Materials and Methods Materials were purchased from the sources listed below.

[0035] Alkyl polyglycosides (APGs) - Two specific APGs from Fenchem Biotek were used. i FM600 / FM1200 - Solid content: 50 wt% in water (CAS: 110615-47-9) with the following composition: C10:<1.0%, C12: 70-76%, C14: 24-30%, and C16:<1.0%. ii FM425N (CAS:68515-73-1&110615-47-9) consisting of: C8: 29-35%, C10: 25-32%, C12: 27-33%, C14: 7-13% and C16: Maximum 1.0%. Sodium methoxide (Sigma-Aldrich, CAS 124-41-4, 95% purity, powder) Ethyl chloroacetate (Sigma-Aldrich, CAS 105-39-5, 99% purity) 3-(Dimethylamino)-1-propylamine (Sigma-Aldrich, CAS-109-55-7, 98% purity) 3-Chloro-2-hydroxypropanesulfonic acid sodium salt (Sigma-Aldrich or Alfa Aesar, PubChem Substance ID 329786196, 98% purity)

[0036] 1 1 H NMR was recorded on a Bruker 400 MHz Spectrometer.

[0037] Unless otherwise stated, all reactions were carried out under a nitrogen atmosphere.

[0038] When provided, conversion values ​​are the percentage of the amount of target product and by-products (if present) relative to the amount of starting material. Yield values ​​are the percentage of the amount of target product alone relative to the amount of starting material.

[0039] Reaction completion was determined by analysis of chloride content and was performed according to APHA method 4500-Cl; method validation was performed to ensure suitability for the surfactant sample matrix.

[0040] Free amine content was analyzed to determine reaction completion and was performed according to ASTM 2074; method validation is underway to ensure suitability for surfactant sample matrices.

[0041] Example 1 Compound 30 was synthesized according to the schematic diagrams in Figures 1 and 2. Alkyl polyglycoside 10 is first subjected to a two-step amination reaction to give tertiary amine intermediate 20. Intermediate 20 is then subjected to a sulfonation reaction to give alkyl polyglycoside-based sultaine 30.

[0042] Synthesis and characterization of 15 Typically, alkyl polyglycoside (FM600 / FM1200; 10; 50 g, 0.1297 mol) and water (50 ml) were added to a four-neck round-bottom flask equipped with a stirrer, thermometer, water-cooled condenser, and nitrogen sparger. 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 approximately 85°C to 90°C and maintained for approximately 4 to 6 hours to form a reaction solution containing 15 (yield: approximately 97%). The reaction was monitored by chloride content analysis and stopped when the theoretical chloride content was reached. The resulting product 15 was 1 It was characterized by 1 H NMR. 1 H 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).

[0043] The formation of 15 1 This was confirmed by the presence of a peak in the 4.1–4.4 ppm region of the H NMR spectrum, which corresponds to the hydrogen present in moiety 14 incorporated into the glycoside.

[0044] Synthesis and characterization of 20 Typically, 3-(dimethylamino)-1-propylamine (16; 12.2 g, 0.1198 mol) was added to the reaction solution containing 15 (approximately 55 g, 0.1261 mol) from the first step. Although sodium methoxide 12 is a reactant / catalyst for forming 20, no additional sodium methoxide 12 was added in this step (i.e., the 12 present in the reaction solution comes from the first step along with 15). The reaction mixture was then heated to approximately 85°C-90°C and maintained for approximately 4-6 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 approximately 0.5 wt%. The resulting product 20 was 1 It was characterized by 1 H NMR. 1H NMR (400MHz, methanol-d4) δ8.56(s,1H),4.79(d,J=3.8Hz,1H),4.27(d,J=7.8Hz,1H),4.00-3.11(m,14H) ),2.45-2.35(m,4H),2.27(s,12H),1.71(p,J=7.3Hz,4H),1.31(d,J=5.5Hz,24H),0.96-0.87(m,3H).

[0045] The formation of 20 was confirmed by the presence of a peak at 8.56 ppm corresponding to a tertiary amine group.

[0046] Synthesis and characterization of 30 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 85-90°C and maintained for about 5-7 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 was reached. The resulting product 30 was 1 It was characterized by 1 H NMR. 1 H NMR (400MHz, methanol-d4) δ8.56(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=5.1Hz,17H),0.95-0.87(m,3H).

[0047] The formation of 30 was confirmed by chemical shifts corresponding to two methyl groups (-CH3) attached to the nitrogen atom between 2.92 and 3.06 ppm and a downfield peak at 3.2 ppm corresponding to a CH-2 next to the nitrogen atom bearing two methyl groups.

[0048] Comparative Example 1 Compound 20 was synthesized from 10 by the procedure of Example 1, except that ethyl chloroacetate (14) was replaced with chloroacetic acid, although this resulted in an exothermic reaction and reduced yields (conversion >80%, yield >74%).

[0049] Without being bound by theory, it is believed that the use of ethyl chloroacetate (14) promotes the site-selective amination at the C6 position of alkyl polyglycosides and reduces the formation of by-products and contaminants.

[0050] Comparative Example 2 As an alternative to 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 low yields and conversions (conversions >75%, yields >70%). Furthermore, 3-dimethylamino-1-propyl chloride hydrochloride is an expensive reactant, making this reaction economically unfeasible.

[0051] Comparative Example 3 3-(Dimethylamino)-1-propylamine (16) can be substituted for chloroamine, however, the use of chloroamine is not economically viable due to its cost.

[0052] Example 2 Performance evaluations of surfactants (including 20) are performed, including foaming, mildness test (Zein test), viscosity thickening, surface tension & CMC, and wetting.

Claims

1. Chemical formula I: 【Chemical 1】 [In the above chemical formula I, R １ is C ８ ~C １６ represents an alkyl group, L １ ~L ３ are each independently C １ ~C ３ represents an alkylene group, R ２ and R ３ are each independently C １ ~C ３ represents an alkyl group, R ４ 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 and n is at least 1. A polymeric amphoteric surfactant compound having the formula:

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

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

4. L １ is CH ２ and / or L ２ (CH ２ ) ３ and / or L ３ is CH ２ 2. The polymeric amphoteric surfactant compound according to claim 1, wherein

5. The chemical formula: 【Chemistry 2】 The polymeric amphoteric surfactant compound according to claim 1, represented by the formula:

6. R １ is C ８ ~C １６ When R is an alkyl group, the polymeric amphoteric surfactant formulation １ or a compound of formula I having a different R １ 10. A polymeric amphoteric surfactant formulation comprising one or more compounds of formula I according to claim 1, formed from a mixture of compounds of formula I having a group.

7. The polymeric amphoteric surfactant compound according to claim 1, or A composition comprising the polymeric amphoteric surfactant blend of claim 6.

8. Formula I: 【Chemistry 3】 1. A method of forming a compound according to claim 1, comprising: The process comprises reacting a compound of formula II: 【Chemistry 4】 to a compound of formula III: 【Chemistry 5】 [In the above formula I, formula II and formula III, R 1 represents a C 8 -C 16 alkyl group; L 1 to L 3 each independently represent a C 1 to C 3 alkylene group; R 2 and R 3 each independently represent a C 1 -C 3 alkyl group; R 4 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 and n is at least 1; X is a leaving group, Y ＋ is a monovalent metal cation. with a compound of formula (I).

9. The compound of formula II can be converted into a compound of formula IV: 【Chemistry 6】 Compounds of formula V: 【Chemistry 7】 [In the above formula IV and formula V, R 1 represents a C 8 -C 16 alkyl group; L 1 and L 2 each independently represent a C 1 -C 3 alkylene group; R 2 and R 3 each independently represent a C 1 -C 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 and n is at least 1; R ９ is H or C １ ~C ３ represents alkyl] 9. The method of claim 8, wherein the compound is formed by reaction of

10. The compound of formula IV can be converted to a compound of formula VI: 【Chemistry 8】 The compound of formula VII: 【Chemistry 9】 [In the above formula VI and formula VII, R 1 represents a C 8 -C 16 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 and n is at least 1; R ９ is H or C １ ~C ３ represents alkyl, X' represents a leaving group; L １’ is a bond or C １ ~C ２ represents an alkylene group] 10. The method of claim 9, wherein the compound is formed by reaction of

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