Polyol-based surfactant

Abstract

The present invention relates to a polyol-based surfactant, more specifically to a biopolyol-based surfactant comprising a naturally derived component, and further relates to a composition comprising same.

Description

polyol surfactants

[0001] According to embodiments of the present invention, it relates to a polyol-based surfactant.

[0002] With very few exceptions, most polyols are derived from petroleum. Considering global warming and environmental concerns, it's necessary to utilize biomass resources, such as plants, rather than petroleum-derived raw materials. Currently, the most widely used polyester polyol is synthesized from adipic acid. However, adipic acid is manufactured using nitric acid oxidation, which creates N2O, a greenhouse gas with a significantly greater global warming effect than CO2. This poses a significant environmental problem.

[0003] In addition, chemically synthesized surfactants are used in cosmetics and cleaning products, and these synthetic surfactants are harmful to the human body, and side effects such as accumulating in the body and promoting cell mutation and skin aging have been reported when used for a long time. Contaminated water generated during the use or synthesis of synthetic surfactants is also emerging as a serious problem, such as pollution of seawater and rivers. Recently, a polyol composition, which is a natural surfactant using anhydrous sugar alcohol, has been reported (Korean Patent Publication No. 2022-000629). However, the technician of the present invention has developed a novel polyol surfactant with surfactant properties in the process of manufacturing a naturally derived polyol compound, and this can provide a bio-polyol surfactant by an eco-friendly manufacturing method.

[0004] The present invention can provide a novel polyol-based surfactant prepared from natural fatty acids or waste oils (e.g., used natural oils) in an environmentally friendly manner.

[0005] The present invention can provide a composition comprising a polyol-based surfactant according to embodiments of the present invention.

[0006] However, the problems to be solved by the present invention are not limited to those mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

[0007] According to embodiments of the present invention, the polyol surfactant may be a compound represented by the following chemical formulas 1 to 4.

[0008] [Chemical Formula 1]

[0009]

[0010] (In the above chemical formula 1

[0011] R is an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester,

[0012] R 1 is A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (having 1 to 3 substituted hydroxyl groups (OH).)

[0013] [Chemical Formula 2]

[0014]

[0015] (In the above chemical formula 2

[0016] R is an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester,

[0017] R 1 Is A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (having 1 to 3 substituted hydroxyl groups (OH).)

[0018] [Chemical Formula 3]

[0019]

[0020] (In the above chemical formula 3

[0021] R and R 2 are each an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester,

[0022] R 1 and R 3 silver Each, A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (the substituted hydroxyl group (OH) is 1 to 3), and n is an integer from 1 to 10.

[0023] [Chemical Formula 4]

[0024]

[0025] (In the above chemical formula 4

[0026] The above R is an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester,

[0027] R 4 and R 5 Each is an alkyl group having 1 to 4 carbon atoms, A+ (cation) (in the case of A+, oxygen (-O-) is -O - (anion) becomes), -(CH2)n-OH (where n is an integer from 1 to 10), -C3H5(OH)2, or (n and m are integers from 1 to 20, respectively), and R 4 and R 5 may be identical or different.

[0028] According to embodiments of the present invention, the polyol-based surfactant may include a polyol-based surfactant represented by Chemical Formula 1 to Chemical Formula 4:

[0029] According to embodiments of the present invention, the composition may include at least one or a combination of two or more of the polyol-based surfactants according to embodiments of the present invention.

[0030] According to one embodiment, the composition may be a detergent composition or a cosmetic composition.

[0031] According to one embodiment, the composition can be used as a surfactant as a polyol.

[0032] According to one embodiment, the composition can also be used as a raw material for manufacturing polyurethane, adhesives, fibers, artificial leather, etc.

[0033] According to one embodiment, the present invention may provide a material or product manufactured using a compound (e.g., a surfactant) or composition according to embodiments of the present invention as a raw material, or a processed product manufactured using the material or product. For example, a polyurethane material or polyester material manufactured using a compound or composition according to embodiments of the present invention as a raw material, or a processed product manufactured using the same, may be provided.

[0034] According to one embodiment, a polyurethane product manufactured from the composition of the present invention may be provided. According to one embodiment, the product may be an insulating material, artificial leather, a matrix, or furniture.

[0035] According to one embodiment, a polyester product manufactured from the composition of the present invention may be provided. According to one embodiment, the product may be a film, fiber, or garment.

[0036] According to one embodiment, the present invention can provide a novel bio-polyol-based surfactant.

[0037] According to one embodiment, the present invention can provide a novel bio-polyol surfactant prepared from naturally occurring fatty acids or waste oils (e.g., used natural oils).

[0038] According to one embodiment, the present invention can provide a bio-polyol surfactant composition comprising a novel bio-polyol surfactant according to the present invention.

[0039] According to one embodiment, the present invention can provide a product or processed product (e.g., a molded body) manufactured using the bio-polyol surfactant of the present invention or a composition thereof as a raw material.

[0040] Hereinafter, embodiments of the present invention will be described in detail. In describing the present invention, detailed descriptions of related, known functions or configurations will be omitted if they are deemed to unnecessarily obscure the gist of the present invention. Furthermore, the terms used in this specification are intended to appropriately express preferred embodiments of the present invention and may vary depending on the intent of the user or operator, or on customary practices in the field to which the present invention pertains. Therefore, definitions of these terms should be based on the overall content of this specification.

[0041] Throughout the specification, when we say that an element is "on" another element, this includes not only cases where the element is in contact with the other element, but also cases where another element exists between the two elements.

[0042] Throughout the specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components.

[0043] In this document, phrases such as "A or B", "at least one of A and B", "at least one of A or B", "A, B, or C", "at least one of A, B, and C", and "at least one of A, B, or C" can each include any one of the items listed together with the corresponding phrase, or all possible combinations thereof. Terms such as "first", "second", or "first" or "second" may be used merely to distinguish the corresponding element from other corresponding elements and do not limit the corresponding elements in any other respect (e.g., importance or order). For example, suitable results may be achieved even if the described techniques are performed in a different order than the described method, and / or the described elements are combined or combined in a different form than the described method, or are replaced or substituted by other elements or equivalents. Therefore, other implementations, other embodiments, and equivalents of the claims are also within the scope of the following claims.

[0044] Hereinafter, the polyol-based surfactant of the present disclosure will be described in detail with reference to examples. However, the present invention is not limited to these examples.

[0045] According to one embodiment, the polyol surfactant of the present disclosure may include a compound represented by the following formulae 1 to 4. The polyol surfactant is prepared from a naturally derived ingredient, and the HLB of the surfactant can be controlled by selectively applying a substituent (e.g., a cationic substituent or a hydrocarbon substituent).

[0046] [Chemical Formula 1]

[0047]

[0048] According to one embodiment, in the above formula 1, R may be selected from an alkane having a hydrocarbon group of 1 to 24 carbon atoms (e.g., an alkyl group); an alkene having a hydrocarbon group of 2 to 24 carbon atoms (e.g., an alkenyl group) or an alkaldiene; or a substituent derived from a fatty acid or fatty acid ester. Preferably, it may be a substituent derived from a fatty acid or fatty acid ester derived from a natural substance.

[0049] In one embodiment, R in the above formula 1 1 is R 1 is A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (having 1 to 3 substituted hydroxyl groups (OH). In the hydroxyalkyl group, the number of hydroxyl groups (-OH) may be 1 to 3.

[0050] [Chemical Formula 2]

[0051]

[0052] According to one embodiment, in the above formula 2, R may be selected from an alkane having a hydrocarbon group of 1 to 24 carbon atoms (e.g., an alkyl group); an alkene having a hydrocarbon group of 2 to 24 carbon atoms (e.g., an alkenyl group) or an alkaldiene; or a substituent derived from a fatty acid or fatty acid ester. Preferably, it may be a substituent derived from a fatty acid or fatty acid ester derived from a natural substance.

[0053] In one embodiment, R in the above chemical formula 2 1 is A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (having 1 to 3 substituted hydroxyl groups (OH). In the hydroxyalkyl group, the number of hydroxyl groups (-OH) may be 1 to 3.

[0054] [Chemical Formula 3]

[0055]

[0056] In one embodiment, R and R in the above chemical formula 3 2 Each of R and R may be selected from an alkane (e.g., an alkyl group) having a hydrocarbon group of 1 to 24 carbon atoms; an alkene (e.g., an alkenyl group) or alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester. Preferably, it may be a substituent derived from a fatty acid or fatty acid ester derived from a natural substance. R and R 2 may be identical or different.

[0057] In one embodiment, R in the above chemical formula 3 1 and R 3 silver Each, A + (A + is an ionic substituent of a cation, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms. In the hydroxyalkyl group, there may be 1 to 3 hydroxyl groups (-OH). R 1 and R 3 may be the same or different from each other. n may be an integer from 1 to 10.

[0058] [Chemical Formula 4]

[0059]

[0060] According to one embodiment, in the above chemical formula 4, R may be selected from an alkane having a hydrocarbon group of 1 to 24 carbon atoms (e.g., an alkyl group); an alkene having a hydrocarbon group of 2 to 24 carbon atoms (e.g., an alkenyl group) or an alkaldiene; or a substituent derived from a fatty acid or fatty acid ester. Preferably, it may be a substituent derived from a fatty acid or fatty acid ester derived from a natural substance.

[0061] In one embodiment, R in the above chemical formula 4 4 and R 5 Each is an alkyl group having 1 to 4 carbon atoms, A+ (cation) (in the case of A+, oxygen (-O-) is -O- (anion) becomes), -(CH2)n-OH (where n is an integer from 1 to 20), -C3H5(OH)2, or (n and m are integers from 1 to 20, respectively). In one embodiment, R 4 and R 5 , may be identical or different.

[0062] According to one embodiment, the above formulae 1 to 4 may provide a polyol-based surfactant optionally applied as follows:

[0063] In one embodiment, R may be a hydrocarbon derived from a natural fatty acid having 12 to 18 carbon atoms.

[0064] According to one embodiment, the R 1 and R 3 can be, respectively, -C2H4-O-C2H4-OH, -C3H6-O-C3H6-OH or -C2H4-O-C4H8-OH.

[0065] According to one embodiment, the R 1 and R 3 are respectively, A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms, for example, -CH3, -C2H5, -C3H7 or -C4H9. The hydroxyalkyl group having 1 to 4 carbon atoms is a monohydric alcohol or polyhydric alcohol in which 1 to 4 hydroxyl groups (-OH) are substituted in the alkyl group, and the substitution position of the hydroxyl group is not limited. For example, -C2H4OH, -C3H6OH, -C4H8OH, -C3H5(OH)2, -C4H7(OH)2, -C4H6(OH)3, -(CH2)n-CH(OH)-CH2-OH (wherein n is an integer from 1 to 2). Preferably, it may be -CH2-CH2-CH2-OH, -CH2-CH(OH)-CH2-OH or -CH2-CH2-CH(OH)-OH. For example, A + (A + is a cation.) is K + , Na + or NH4 + It could be.

[0066] According to one embodiment, the R 4 and R 5 are each an alkyl group having 1 to 4 carbon atoms, -(CH2)n-OH (n is 1), -C3H5(OH)2 or , and preferably, n and m may each be 1 to 8. For example, it may be -C4H8-O-C4H8-OH, -C4H8-OH, -C3H6-O-C3H6-OH, -C3H6-OH, -C2H4-O-C2H4-OH, or -C2H4-OH.

[0067] In one embodiment, the "n" and "m" may each be an integer from 1 to 20; an integer from 1 to 10; an integer from 1 to 8; an integer from 1 to 5; an integer from 1 to 4; an integer from 1 to 3, or an integer from 1 to 2.

[0068] In one embodiment, the "A+" may be an alkali metal cation, an ammonium cation (NH4+), an organic ammonium cation, a sulfonium cation, a diazonium cation, a pyridinium cation, a phosphonium cation, or a pyridinium cation. For example, the alkali metal cation may be K+, Na+, Li+, or the like.

[0069] According to one embodiment, the "hydrocarbon" may be a hydrocarbon having 1 to 28 carbon atoms; 2 to 28 carbon atoms; 3 to 22 carbon atoms; 10 to 22 carbon atoms; 16 to 22 carbon atoms; 4 to 20 carbon atoms; 4 to 18 carbon atoms; 4 to 14 carbon atoms; or 4 to 12 carbon atoms; 4 to 10 carbon atoms or 1 to 4 carbon atoms. For example, the hydrocarbon may be a saturated or unsaturated hydrocarbon group (e.g., an unsaturated fatty acid).

[0070] According to one embodiment, the "fatty acid" is caprylic acid, capric acid, lauric acid, myristic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, pentadecanoic acid, palmitic acid, arachidonic acid, myristoleic acid, palmitoleic acid, sapienic acid, elaidic acid, vaccenic acid; It can be oleic acid (a monounsaturated omega-9 fatty acid), eicosenoic acid (a monounsaturated omega-9 fatty acid), erucic acid (a monounsaturated omega-9 fatty acid), arachidonic acid (a polyunsaturated omega-6 fatty acid), eicosenoic acid (an omega-6 fatty acid, 11,14,17-Eicosatrienoic acid), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), linoleic acid (a polyunsaturated omega-6 fatty acid), linoleidic acid (an omega-6 trans fatty acid), or α-linolenic acid (ALA).

[0071] According to one embodiment, the polyol surfactant may be selected from compounds represented by the following chemical formulas:

[0072] ,

[0073] ,

[0074] ,

[0075] ,

[0076] ,

[0077] ,

[0078] and

[0079]

[0080] In one embodiment, the polyol surfactant is R 1 , R 3 , R 4 or R 5 It may have an HLB of 12 or higher by applying an ionic substituent (e.g., a cationic substituent) to at least one of them.

[0081] In one embodiment, the polyol surfactant is R 1 , R 3 , R 4 or R 5 It may have an HLB of 3 or less by applying a hydrocarbon-based substituent to at least one of the compounds.

[0082] In one embodiment, the polyol surfactant is R 1 , R 3 , R 4 or R 5By applying a hydroxyalkyl group to at least one or more of the above, it can have an HLB of 3 or more and 12 or less; or 6 or more and 12 or less. For example, when a polyhydric alcohol (e.g., a hydroxyalkyl group having two or more hydroxyl groups) is applied without introducing a cationic substituent into the molecule, it can exhibit an HLB of 6 to 12. For example, when a monohydric alcohol (e.g., a hydroxyalkyl group having one hydroxyl group) is introduced, a surfactant having an HLB of less than 6 (e.g., chemical formula 4) can be provided.

[0083] According to one embodiment, the molecular weight (g / mol, M) of the polyol surfactant W Or Mn) can be 5,000 or less; 3,000 or less; 2,000 or less; 1,900 or less; 1,800 or less; 1,600 or less; 1,400 or less; 1,200 or less; 1,000 or less; 800 or less; or 100 or more; 300 or more; 400 or more; 700 or more; 900 or more; 1,100 or more; 1,500 or more.

[0084] According to one embodiment, the light transmittance of the polyol-based interfacial compound represented by the above chemical formula 1 may be 50% or more; 60% or more; 70% or more; 80% or more; or 90% or more. The light transmittance may be related to a wavelength of 400 nm to 600 nm.

[0085] According to one embodiment, the polyol surfactant can be applied as a component of a synthetic process, such as a raw material, formulation, dispersant, coating agent, or phase stabilizer.

[0086] According to one embodiment, the present invention can provide a composition comprising a polyol-based surfactant according to embodiments of the present invention.

[0087] According to one embodiment, the composition may include two or more polyol surfactants according to embodiments of the present invention, which are distinguished by HLB. For example, when two or more polyol surfactants are applied, two or more polyol surfactants having different HLB values ​​may be applied. For example, the two or more polyol surfactants include a polyol surfactant having an HLB of 12 or more (i.e., a first polyol surfactant) and a polyol surfactant having an HLB of 12 or less (or less) (i.e., a second polyol surfactant); and have different HLB values.

[0088] According to one embodiment, the "HLB" is a hydrophilic-lipophilic balance value, which is a measure of the degree of hydrophilicity to lipophilicity of a surfactant. The HLB value is generally in the range of 0 to 20, with an HLB value of 0 indicating highly lipophilic properties and an HLB value of 20 indicating highly hydrophilic properties. The HLB can be measured and calculated by methods generally known in the art. For example, the Griffin, Davis calculation method, HLB = [EХP] / 5 (E: weight (%) of polyoxyethylene in the molecule and P: weight (%) of polyhydric alcohol in the molecule), etc. can be used. In addition, when applying a mixed surfactant, the HLB value of the surfactant mixture can be calculated as follows. HLB A (Fraction of surfactant A) + HLB B (Fraction of surfactant B) = HLB A+B 혼합물

[0089] According to one embodiment, the composition may be in the form of a solid (e.g., powder, crystal, film, bead, plastic, etc.), a semi-solid (e.g., gel), an emulsion, a suspension, a liquid, etc.

[0090] In one embodiment, the composition may be a detergent composition or a cosmetic composition. For example, it may be a human detergent (i.e., a detergent applied to all parts except the body; e.g., a scalp / hair cleanser, a face cleanser, a mouthwash, a body cleanser, a soap, etc.), a household detergent (e.g., a detergent for cleaning hard substrates (i.e., a detergent for cleaning wood, alloys, polymers, plastics, ceramics, etc.); e.g., a laundry detergent, a kitchen detergent, a toilet cleaner, a bathroom cleaner, a car detergent), an industrial detergent, etc. For example, the cosmetic composition may be a composition for the face, nails, lips, scalp, and body, and more specifically, it may be a lotion, a skin, a balm, a cream, a gel, etc.

[0091] According to one embodiment, the polyol surfactant represented by the above chemical formula 1 may be present in the composition in an amount of 1 wt% to 100 wt%, 1 wt% to 99 wt%, 1 wt% to 90 wt%, or 10 wt% to 50 wt%, or 10 wt% to 30 wt%.

[0092] According to one embodiment, the composition may appropriately select and add active ingredients, functional ingredients, solvents, oils, fragrances, etc. according to the intended use, and these are not specifically mentioned in this document.

[0093] According to one embodiment, the present invention may provide a material or product manufactured using a compound (e.g., a surfactant) or composition according to embodiments of the present invention as a raw material, or a processed product manufactured using the material or product. For example, a polyurethane material manufactured using a compound or composition according to embodiments of the present invention as a raw material, or a processed product manufactured using the same, may be provided. For example, a polyester material manufactured using a compound or composition according to embodiments of the present invention as a raw material, or a processed product manufactured using the same, may be provided.

[0094] According to one embodiment, the composition may be a polyurethane-based composition or a polyester-based composition. For example, it may be used as a raw material for the synthesis of polyurethane or a polyurethane-containing composition. For example, it may be used as a raw material for the synthesis of polyester or a polyester-containing composition.

[0095] According to one embodiment, the composition can provide a polyurethane product manufactured from a polyurethane-based composition. For example, it can provide processed products such as insulation materials, artificial leather, mattresses, and furniture.

[0096] According to one embodiment, the composition may provide a polyester product made from the polyester composition. For example, the product may be a film, fiber, garment, or the like made from the polyester composition.

[0097] According to one embodiment, the composition can also be used as a raw material for polyurethane-based molded articles, polyester-based molded articles, adhesives, fibers, artificial leather, etc.

[0098] According to one embodiment, the polyol-based surfactant represented by the above Chemical Formulas 1 to 4 may be reacted in the presence of a reaction raw material and a catalyst (e.g., an alkaline catalyst) at a temperature of room temperature to 300°C; room temperature to 280°C; room temperature to 250°C; room temperature to 230°C; room temperature to 200°C; room temperature to 180°C; room temperature to 150°C; 50°C to 100°C; or 70°C to 90°C for 30 minutes or more; 1 hour or more; 5 hours or more; 10 hours or more; 15 hours or more; or 20 hours or more. The above-mentioned time may be appropriately selected in consideration of the reaction completion time. After completion of the reaction, the desired product may be obtained using a process known in the technical field of the present invention, such as cooling, separation (filtration, extraction, etc.), washing, recrystallization, chromatography, drying, etc., which is not specifically mentioned in this document.

[0099] According to one embodiment, the structure of the target product can be determined using analytical methods known in the art of the present invention, such as IR, NMR, XRD, XPS, molecular weight (GPC, MASS, etc.), which are not specifically mentioned in this document.

[0100] Example

[0101] A compound of the following chemical formula was synthesized by applying a natural fatty acid and glycerol in a molar ratio of 1:2 and reacting at 230°C for 4 hours in the presence of an alkaline catalyst. The structure of the desired product was confirmed through IR, NMR, and mass spectrometry.

[0102] [compound]

[0103]

[0104] Although the embodiments described above have been described in terms of limited embodiments, those skilled in the art will appreciate that various modifications and variations can be made based on the above teachings. For example, appropriate results can still be achieved if the described techniques are performed in a different order than described, and / or the described components are combined or combined in a different manner than described, or are replaced or substituted with other components or equivalents. Therefore, other implementations, other embodiments, and equivalents of the claims also fall within the scope of the claims described below.

Claims

1. Polyol surfactants represented by the following chemical formulas 1 to 4: [Chemical Formula 1] (In the above chemical formula 1 R is an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester, R 1 is A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (having 1 to 3 substituted hydroxyl groups (OH).) [Chemical Formula 2] (In the above chemical formula 2 R is an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester, R 1 is A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (having 1 to 3 substituted hydroxyl groups (OH).) [Chemical Formula 3] (In the above chemical formula 3 R and R 2 are each an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester, R 1 and R 3 silver Each, A + (A + is a cation), an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms (the substituted hydroxyl group (OH) is 1 to 3), and n is an integer from 1 to 10. [Chemical Formula 4] (In the above chemical formula 4 The above R is an alkane having a hydrocarbon group of 1 to 24 carbon atoms; an alkene and alkaldiene having a hydrocarbon group of 2 to 24 carbon atoms; or a substituent derived from a fatty acid or fatty acid ester, R 4 and R 5 Each is an alkyl group having 1 to 4 carbon atoms, A+ (cation) (in the case of A+, oxygen (O) is -O - (anion) becomes), -(CH2)n-OH (where n is an integer from 1 to 10), -C3H5(OH)2, or (n and m are integers from 1 to 20, respectively), and R 4 and R 5 are identical or different from each other.) 2. In paragraph 1, In the above chemical formulas 1 to 3 The above R 1 and R 3 are respectively -C2H4-O-C2H4-OH, -C3H6-O-C3H6-OH or -C2H4-O-C4H8-OH, The above R 1 and R 3 are respectively, A + (A + A polyol-based surfactant, wherein the alkyl group having 1 to 4 carbon atoms, or the hydroxyalkyl group having 1 to 4 carbon atoms (the number of substituted hydroxyl groups (OH) is 1 to 2).

3. In paragraph 1, In the above chemical formula 4 The above R is a hydrocarbon derived from a natural fatty acid having 12 to 18 carbon atoms, The above R 4 and R 5 Each is an alkyl group having 1 to 4 carbon atoms, -(CH2)n-OH (n is an integer from 1 to 4), -C3H5(OH)2 or (n is an integer from 1 to 4, and m is an integer from 1 to 20.) A polyol surfactant.

4. In paragraph 1, A in the above chemical formulas 1 to 4 + A polyol-based surfactant, wherein each of the cations is an alkali metal cation, an ammonium cation, an organic ammonium cation, a sulfonium cation, a diazonium cation, a pyridinium cation, a phosphonium cation, or a pyridinium cation.

5. In paragraph 1, A polyol-based surfactant having a molecular weight (g / mol) of 5,000 or less.

6. In paragraph 1, The above polyol-based surfactant contains A+ (cation) and has an HLB of 12 or more.

7. In paragraph 1, The above polyol-based surfactant does not contain A+ (cation) and has an HLB of 12 or less.

8. At least one of the polyol surfactants of paragraph 1 A composition comprising:

9. In paragraph 8, The above polyol surfactant comprises two or more types, The above polyol surfactant is, A first polyol surfactant having HLB 12 or higher and A second polyol surfactant having an HLB of 12 or less (but having a different HLB from the first polyol surfactant) A composition comprising:

10. In paragraph 8, The above polyol surfactant is, A composition comprising 0.01 wt% to 50 wt% of the above composition.

11. In paragraph 8, The above composition, A composition, which is a detergent composition or a cosmetic composition.

12. In paragraph 8, The above composition, A composition applied to a polyurethane material or a processed product thereof; or a polyester material or a processed product thereof.

13. A polyurethane product manufactured using the composition of Article 8.

14. In paragraph 13, The above product is a polyurethane product, which is an insulation material, artificial leather, matrix or furniture.

15. A polyester product manufactured using the composition of Article 8.

16. In paragraph 15, The above product is a polyester product, which is a film, fiber or garment.

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