Novel surfactant compounds

Abstract

The present invention relates to novel surfactant compounds. The invention relates to a novel surfactant compound, in particular to a novel Guerbet type surfactant compound which shows excellent surfactant performance.

Description

TECHNICAL FIELD

[0001] The present invention relates to novel surfactant compounds. In particular, novel Guerbet-type surfactant compounds. BACKGROUND

[0002] Surfactants are molecules that have both hydrophobic and hydrophilic groups. This property allows surfactants to simultaneously bind to both oil and water, thereby reducing the surface tension of, for example, water. A wide variety of synthetic surfactants exist today, which can be used for different purposes.

[0003] Surfactants can be divided into four major categories, including amphoteric (or zwitterionic), anionic, cationic, and non-ionic surfactants.

[0004] Zwitterionic surfactants contain both positively and negatively charged head groups, and are interesting molecules due to their many unique properties. Generally, they are mild to the skin and eyes, low in toxicity, water-soluble, have a wide range of isoelectric points, high foam stability, resistant to hard water, and can be degraded by oxidizing agents. Factors that influence zwitterionic surfactants to varying degrees include, but are not limited to, temperature, pH, and added electrolytes.

[0005] Cationic surfactants are surfactants with a positively charged functional group (hydrophilic head), while anionic surfactants are surfactants with a negatively charged functional group (hydrophilic head).

[0006] Guerbet alcohols are a class of compounds named after the French chemist Marcel Guerbet, who first discovered them in 1899. Guerbet was studying the reaction of alcohols with metallic sodium when he discovered a new class of alcohols with branched structures. He later found that these branched alcohols could be used as surfactants.

[0007] In the early 20th century, Guerbet alcohols were primarily used as solvents and intermediates for the synthesis of other compounds. It was not until the 1950s that their surfactant properties were fully recognized and they began to be used in a range of industrial applications. Guerbet-type surfactants gained increasing popularity in the 1970s and 1980s as more industries discovered their unique properties. The branched structure and unique functional groups of Guerbet-type surfactants impart excellent surface activity and stability, making them highly effective at reducing surface tension and stabilizing emulsions.

[0008] Guerbet-type surfactants continued to be popular in the 1990s and early 21st century as advances in technology and chemistry allowed for the development of new Guerbet-type surfactant formulations with improved properties.

[0009] Due to their versatile properties, they are used in a variety of industries, including but not limited to detergents, personal care products, pharmaceuticals, agricultural chemicals, mining, metalworking, papermaking, lubricating products, latex systems, plastics, and composites.

[0010] In terms of market size for surfactants, the global surfactants market was valued at $33 billion in 2020 and is expected to grow at a CAGR of 3.5% between 2021-2027, reaching $44 billion by the end of 2027. Interestingly, goupert surfactants are expected to grow from $1.1 billion in 2021 to $1.4 billion in 2029, with a CAGR of 3.9%. During the forecast period, the cosmetics and personal care market is expected to be the main driver of the global goupert alcohol market, with the Asia Pacific region leading the market. During this period, it is expected that the market share of anionic amino acid surfactants will be replaced by cationic surfactants and zwitterionic surfactants.

[0011] The unique properties of goupert surfactants make them valuable and useful in many industries, and they have the potential to expand further as research and technology develop. However, goupert surfactants have a unique chemical structure consisting of branched alkyl chains, which makes their manufacture more challenging compared to other surfactants with straight-chain alkyl chains. This complexity in structure requires specialized production processes and equipment, which can result in higher production costs and lower yields. As a result, goupert surfactants may be in limited supply, and they may not be as widely available as other types of surfactants.

[0012] The limited availability of goupert surfactants also makes them more expensive to obtain. The higher production costs associated with manufacturing these surfactants can translate into higher prices for consumers. Additionally, because their production may not be as large as other surfactants, suppliers may need to charge extra fees for goupert surfactants to cover their costs and remain profitable.

[0013] The limited supply of goupert surfactants also presents logistical challenges for companies that rely on these surfactants in their products. Companies may need to establish relationships with specialized suppliers or invest in their own production capabilities to ensure a steady supply of goupert surfactants. Furthermore, some goupert surfactants have only been available for licensing from patent holders, which is obviously very expensive. These additional costs and challenges can make it more difficult for some companies to use goupert surfactants and may limit their use in niche applications or high-end products.

[0014] Despite the growing trend in demand for bio-based surfactants, the high cost of manufacturing these surfactants negatively impacts the expected growth of the market. Bio surfactants are more expensive compared to traditional synthetic surfactants. The high cost of producing bio surfactants is driven by the high cost of raw materials and offsets the economies of scale of bio surfactants. This is especially true for fast-moving consumer goods (FMCG) companies such as Reckitt Benckiser, P&G, L’Oreal and Colgate, where raw material prices have a direct impact on consumer goods. For these reasons, there is a huge demand for synthetic surfactants.

[0015] In view of the above, the unique chemical structure and specialized production process associated with the Gobert-type surfactants makes them more expensive and harder to obtain than other types of surfactants, which limits their availability and use in certain applications. Therefore, there is a clear need in the art for new surfactants, particularly new Gobert-type surfactants, that are less expensive to synthesize.

[0016] Object of the present invention Therefore, it is an object of the present invention to provide new surfactant compounds, particularly new Gobert-type surfactant compounds, that at least partially overcome the above-mentioned drawbacks and limitations, and / or that provide a useful alternative to the prior art, mitigating the high cost of manufacturing the Gobert-type surfactants currently used. SUMMARY

[0017] According to a first aspect of the present invention, there is provided a new surfactant compound having the following chemical structure:

[0018] wherein: (i) X is COR or CH2R, wherein R is R’CH(CH2)2R’ or R’CCHCH2R’, wherein R’ is C n H 2n+1 (n = 1, 2,...); (ii) Y is selected from the group consisting of: H; R’, X; (CH2) n CO2M (n = 0, 1, 2,...; M = H, R’, Li, Na, K, Rb, Cs, Fr, Er, Gd,...); (CH2) n A (n = 0, 1, 2,...; A = OH, OR’, SH, SR’, NH2, NHR’, NR’2, CONH2, CONHR’, CONR’2, aromatic group, heteroaromatic group, halogen (F, Cl, Br, I)); or CH2CH(CH3)O(CH2CH2O)n H (n = 0, 1, 2,...); and (iii) Z is selected from the group consisting of: H; R'; (CH2) n CO2M (n = 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...); CH2CH(CH3)0(CH2CH20) n H (n = 0, 1, 2,...); or (CH2) n A (n = 0, 1, 2,...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, an aromatic group, a heteroaromatic group, a halogen (F, Cl, Br, I)).

[0019] According to a second aspect of the present invention, there is provided a new surfactant compound having the following chemical structure:

[0020] wherein: (i) X is COR or CH2R, wherein R is R'CH(CH2)2R' or R'CCHCH2R', wherein R' is C n H 2n+1 (n = 1, 2,...); (ii) Y is selected from the group consisting of: H; R', X; (CH2) n CO2M (n = 0, 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...); (CH2) n A (n = 0, 1, 2,...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, an aromatic group, a heteroaromatic group, a halogen (F, Cl, Br, I)); or CH2CH(CH3)0(CH2CH20) n H (n = 0, 1, 2,...); and (iii) Z is selected from the group consisting of: H; R'; (CH2) n A (n = 0, 1, 2,...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, an aromatic group (e.g. C6H5, C6H4OH), a heteroaromatic group, a halogen (F, Cl, Br, I)); (CH2) n CO2M (n = 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...);

[0021] or

[0022] wherein A = OH (SER); SH (CYS); CH2SMe (MET); COOH (ASP); CH2COOH (GLU); (CH2)3NH2 (LYS); CONH2 (ASP); CH2CONH2 (GLN); CH(OH)Me (THR); and wherein ALA = alanine; ASP = aspartic acid; GLU = glutamic acid; GLY = glycine; IDA = iminodiacetic acid; VAL = valine; LEU = leucine; ILE = isoleucine; PHE = phenylalanine; SER = serine; CYS = cysteine; MET = methionine; LYS = lysine; GLN = glutamine; THR = threonine.

[0023] According to a third aspect of the present application, there is provided a novel surfactant compound having the following chemical structure:

[0024] wherein: (i) X is COR or CH2R, wherein R is R'CH(CH2)2R' or R'CCHCH2R', wherein R' is C n H 2n+1 (n = 1, 2,...); (ii) D is selected from the group consisting of: O; N(CH2) n A or N(C6H4) n A (n = 0, 1, 2,...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, an aromatic group (e.g. C6H5, C6H4OH), a heteroaromatic group, or a halogen (F, Cl, Br, I)); and (iii) Z is selected from the group consisting of: H; R'; N(CH2) n A (n = 0, 1, 2,...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, an aromatic group (e.g. C6H5, C6H4OH), a heteroaromatic group, a halogen (F, Cl, Br, I)); or (CH2) nCO2M (n = 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...).

[0025] According to a fourth aspect of the present application, there is provided a new surfactant compound having the following chemical structure:

[0026] wherein: (i) X is COR or CH2R, wherein R is R'CH(CH2)2R' or R'CCHCH2R', wherein R' is C n H 2n+1 (n = 1, 2,...); (ii) D is selected from the group consisting of: O; N(CH2) n A or N(C6H4) n A (n = 0, 1, 2,...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, an aromatic group (e.g. C6H5, C6H4OH), a heteroaromatic group, or a halogen (F, Cl, Br, I)); and (iii) Z is selected from the group consisting of: H; R'; N(CH2) n A (n = 0, 1, 2,...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, an aromatic group (e.g. C6H5, C6H4OH), a heteroaromatic group, a halogen (F, Cl, Br, I)); or (CH2) n CO2M (n = 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...).

[0027] The above and other features, aspects, and advantages of the present application will become more apparent from the following detailed description, which illustrates, by way of example, the principles of the application. This description is given for the sake of example only, and without intending to limit the scope of the application. DETAILED DESCRIPTION

[0028] The disclosed subject matter will now be described more fully with reference to the accompanying drawings, in which representative embodiments are shown. The disclosed subject matter may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and fully convey the scope of the embodiments to those skilled in the art. Non-limiting examples of preferred embodiments of the present application are described in more detail below.

[0029] Example 1 The surfactant compounds according to the present application can be synthesized according to the following synthetic routes.

[0030] AC = aldol condensation AH = acid hydrolysis Am = amidation [dH] = dehydrogenation E = esterification (M = R) G = Grignard reaction HAM = hydroaminomethylation HC = hydrocyanation HF = hydroformylation [H] = hydrogenation MC = methoxycarbonylation [O] = oxidation OM = olefin (alkene) metathesis (i) = reductive amination (ii) = amidation via acyl halide D = O, NH (1-x) R x M = metal, alkyl R, R', R" = alkyl, etc.

[0031] X = CH2(amines), C=O (amides) The source of the olefin (alkene) can be industrial (i.e. Fischer-Tropsch synthesis, ethylene oligomerization, alkane (paraffin) cracking, alkyne hydrogenation, etc.) or natural (i.e. oil and fat chemicals, sugars, etc.).

[0032]

[0033] The surfactant compounds according to the first aspect of the present application synthesized from the above synthetic routes are shown in Table 1 below.

[0034] Table 1: Surfactant compounds according to the first aspect of the present application

[0035] The surfactant compounds according to the second aspect of the present application synthesized from the above synthetic routes are shown in Table 2 below.

[0036] Table 2: Surfactant compounds according to the second aspect of the present invention

[0037] The surfactant compounds of the third aspect of the present invention synthesized by the above synthetic route are shown in Table 3 below.

[0038] Table 3: Surfactant compounds according to the third and fourth aspects of the present invention

[0039] As shown in Table 4, the surfactant compounds according to the first, second, third and fourth aspects of the present invention exhibit the following surfactant properties.

[0040] Table 4: Surfactant Properties

[0041] As can be seen from the above results, surfactant compounds according to the first and second aspects of the present invention have been synthesized, which exhibit superior surfactant properties compared with known surfactants.

[0042] This description is given by way of example only, and is intended to provide a description that is considered most useful and readily understood in relation to the principles and concepts of the invention. In this respect, no attempt is made to show structural details of the invention and / or the apparatus used therein, except as necessary for a basic understanding of the invention.

Claims

1. Novel surfactant compounds having the following chemical structures: in: (i) X is COR or CH2R, where R is R'CH(CH2)2R' or R'CCHCH2R', where R' is C n H 2n+1 (n=1, 2, ...); (ii) Y is selected from the group consisting of the following items: H; R', X; (CH2) n CO2M (n = 0, 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...); (CH2) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic group, heteroaromatic group, halogen (F, Cl, Br, I)); or CH2CH(CH3)O(CH2CH2O) n H(n = 0, 1, 2, ...); and (iii) Z is selected from the following groups: H; R'; (CH2) n CO2M (n = 1, 2,…; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,…); CH2CH(CH3)O(CH2CH2O) n H (n = 0, 1, 2, ...); or (CH2) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic groups, heteroaromatic groups, halogens (F, Cl, Br, I)).

2. Novel surfactant compounds with the following chemical structures: in: (i) X is COR or CH2R, where R is R'CH(CH2)2R' or R'CCHCH2R', where R' is C n H 2n+1 (n=1, 2, ...); (ii) Y is selected from the group consisting of the following items: H; R', X; (CH2) n CO2M (n = 0, 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...); (CH2) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic group, heteroaromatic group, halogen (F, Cl, Br, I)); or CH2CH(CH3)O(CH2CH2O) n H(n = 0, 1, 2, ...); and (iii) Z is selected from the following groups: H; R'; (CH2) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic groups (e.g., C6H5, C6H4OH), heteroaromatic groups, halogens (F, Cl, Br, I)); (CH2) n CO2M (n = 1, 2,...; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,...); or Where A = OH (SER); SH (CYS); CH2SMe (MET); COOH (ASP); CH2COOH (GLU); (CH2)3NH2 (LYS); CONH2 (ASP); CH2CONH2 (GLN); CH(OH)Me (THR); and Where ALA = alanine; ASP = aspartic acid; GLU = glutamic acid; GLY = glycine; IDA = iminodiacetic acid; VAL = valine; LEU = leucine; ILE = isoleucine; PHE = phenylalanine; SER = serine; CYS = cysteine; MET = methionine; LYS = lysine; GLN = glutamine; THR = threonine.

3. Novel surfactant compounds with the following chemical structures: in: (i) X is COR or CH2R, where R is R'CH(CH2)2R' or R'CCHCH2R', where R' is C n H 2n+1 (n=1, 2, ...); (ii) D is selected from the following groups: O; N(CH2) n A or N (C6H4) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic groups (e.g., C6H5, C6H4OH), heteroaromatic groups, or halogens (F, Cl, Br, I)); and (iii) Z is selected from the following groups: H; R'; N(CH2) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic groups (e.g., C6H5, C6H4OH), heteroaromatic groups, halogens (F, Cl, Br, I)); or (CH2) n CO2M (n = 1, 2,…; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,…).

4. Novel surfactant compounds with the following chemical structures: in: (i) X is COR or CH2R, where R is R'CH(CH2)2R' or R'CCHCH2R', where R' is C n H 2n+1 (n=1, 2, ...); (ii) D is selected from the following groups: O; N(CH2) n A or N (C6H4) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic groups (e.g., C6H5, C6H4OH), heteroaromatic groups, or halogens (F, Cl, Br, I)); and (iii) Z is selected from the following groups: H; R'; N(CH2) n A (n = 0, 1, 2, ...; A = OH, OR', SH, SR', NH2, NHR', NR'2, CONH2, CONHR', CONR'2, aromatic groups (e.g., C6H5, C6H4OH), heteroaromatic groups, halogens (F, Cl, Br, I)); or (CH2) n CO2M (n = 1, 2,…; M = H, R', Li, Na, K, Rb, Cs, Fr, Er, Gd,…).

5. The novel surfactant compound according to claim 1, wherein the surface tension at the critical micelle concentration (CMC) is from 27.37 mN / m to 30.71 mN / m.

6. The novel surfactant compound according to claim 2, wherein the surface tension at the critical micelle concentration (CMC) is from 25.20 mN / m to 33.64 mN / m.

7. The novel surfactant compound according to claim 1 or claim 5, wherein X is CH2R, wherein R is R'CH(CH2)2R', and R' is C n H 2n+1 (n=4, 6, 7, 8); Y is CH2CO2M (M = Na); and Z is CH2CO2M (M = Na).

8. The novel surfactant compound according to claim 1 or claim 5, wherein X is COR, wherein R is R'CH(CH2)2R', and R' is C n H 2n+1 (n = 4, 6); Y is CH2CO2M (M = Na); and Z is CH2CO2M (M = Na).

9. The novel surfactant compound according to any one of claims 1, 5, 8 or 9, wherein X is preferably CH2R, wherein R is R'CH(CH2)2R', and R' is C n H 2n+1 (n = 7, 8); Y is preferably CH2CO2M (M = Na); and Z is preferably CH2CO2M (M = Na).

10. The novel surfactant compound according to claim 2 or claim 6, wherein X is CH2R, wherein R is R'CH(CH2)2R', and R' is C n H 2n+1 (n=4, 6, 7, 8); Y is H; and Z is CH2CO2M (M = Na).

11. The novel surfactant compound according to claim 2 or claim 6, wherein X is COR, wherein R is R'CH(CH2)2R', and R' is C n H 2n+1 (n=4, 6, 7); Y is H; and Z is H, CH3, (CH2). n CO2M (n = 1, 2; M = Na).

12. The novel surfactant compound according to any one of claims 2, 6, 10 or 11, wherein X is preferably CH2R, wherein R is R'CH(CH2)2R', and R' is C n H 2n+1 (n = 9); Y is preferably H; and Z is preferably CH2CO2M (M = Na).

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