Multi-branched surfactants and methods of making the same

Abstract

The present invention relates to a multi-branched surfactant and a method for making the same. The multi-branched surfactant is made by ring-opening reaction of a mixture. The mixture comprises core reactants and branch reactants, wherein the core reactants comprise a polyol compound and a polyamine compound, and the branch reactants comprise a compound having an epoxy group. The multi-branched surfactant has good interfacial properties and compatibility, and is not easy to precipitate.

Description

Technical Field

[0001] This invention relates to a surfactant, and more particularly to a multibranched surfactant with a multibranched structure and a method for preparing the same. Background Technology

[0002] By adjusting the hydrophilic-lipophilic balance, surfactants can exhibit excellent interfacial properties. Some surfactants with special structures or functional groups can effectively eliminate foam, and therefore are often added to solutions to inhibit foam formation. Generally, surfactants used as defoamers can be classified into silicone-type defoamers containing siloxane bonds, and non-silicone-type defoamers such as polyethers, alcohols, or fatty acid esters.

[0003] Among them, silicone defoamers have better defoaming properties compared to non-silicone defoamers. However, when using silicone defoamers, the high temperature environment can easily destroy the dispersion stability of the groups in water. Therefore, silicone surfactants are prone to migration and stratification, which reduces compatibility and leads to precipitation over time. As a result, end products containing silicone surfactants are prone to surface defects such as blurred appearance, fish eyes, or oil spots.

[0004] Although non-silicone defoamers are less prone to precipitation, they generally lack siloxane bonds, resulting in poor defoaming properties. Therefore, they are only suitable for applications with mild foaming characteristics and are not effective at eliminating dense foams. Furthermore, non-silicone defoamers generally have poor acid and alkali resistance, low-temperature flowability, and cold resistance. Consequently, the application areas of non-silicone defoamers are relatively limited.

[0005] In view of this, there is an urgent need to provide a multibranched surfactant, its preparation method and a surfactant solution containing it, so as to further improve the interfacial properties of the surfactant and solve the defects of traditional surfactants, their preparation methods and surfactant solutions containing them. Summary of the Invention

[0006] Therefore, one aspect of the present invention is to provide a multibranched surfactant having a specific multibranched structure, thereby exhibiting better interfacial activity and compatibility, and having modifiable terminal groups to enhance its applicability.

[0007] Another aspect of the present invention is to provide a method for preparing a multibranched surfactant, which is prepared by reacting a mixture.

[0008] According to one aspect of the present invention, a multibranched surfactant is proposed having the structure shown in formula (I).

[0009]

[0010] In formula (I), X represents a polyol group or polyamine group with 2 to 20 carbon atoms, R represents the structure shown in formula (I-1) below, and q represents an integer not less than 2.

[0011]

[0012] In formula (I-1), R1, R2, and R3 independently represent hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, methylalkyl ethers with 1 to 20 carbon atoms, methylaryl ethers with 6 to 25 carbon atoms, methylalkenyl ethers with 2 to 4 carbon atoms, alkylphenol groups, aromatic phenol groups, or alkenyl groups with 1 to 20 carbon atoms, respectively; x, y, and z independently represent 0 to 30, and the sum of x, y, and z is 1 to 90; "*" represents the position of the bond between formula (I-1) and the oxygen atom of the polyol group or the nitrogen atom of the polyamine group.

[0013] According to some embodiments of the present invention, the aforementioned polyol group or polyamine group has 2 to 10 hydroxyl or amino groups, and q represents an integer from 2 to 10.

[0014] According to some embodiments of the present invention, the aforementioned amino group comprises primary amines and / or secondary amines.

[0015] According to some embodiments of the present invention, the aforementioned R1, R2 and R3 are not the same as each other.

[0016] According to another invention of the present invention, a method for preparing a multibranched surfactant is provided. The method involves performing a ring-opening reaction on a mixture to prepare the multibranched surfactant. The mixture comprises a core reactant and branch reactants. The core reactant comprises a polyol compound or a polyamine compound having 2 to 20 carbon atoms, while the branch reactant comprises a compound having one epoxy group.

[0017] According to some embodiments of the present invention, the amount of the aforementioned nuclear reactant is 1 mole, and the amount of the branching reactant is at least 2 moles.

[0018] According to some embodiments of the present invention, the aforementioned compound having an epoxy group has the structure shown in formula (II).

[0019]

[0020] In formula (II), Y represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkyl ether having 1 to 20 carbon atoms, an aromatic ether having 6 to 25 carbon atoms, an alkenyl ether having 2 to 4 carbon atoms, an alkylphenol group, an aromatic phenol group, or an olefin group having 1 to 20 carbon atoms.

[0021] According to some embodiments of the present invention, the aforementioned multibranched surfactant has the structure shown in formula (III).

[0022]

[0023] In formula (III), X1 represents an n-valent group with 2 to 20 carbon atoms, and X1 has n2 secondary amines, where n1 and n2 independently represent integers from 0 to n, and the sum of n1 and n2 is n; X2 represents -O-* or And “*” represents the position of the bond with R; R″ is bonded to the nitrogen atom of the secondary amine of X1; R′ and R″ respectively independently represent the structure shown in equation (III-1); n represents an integer not less than 2. When n1 and n2 independently represent integers not less than 2, multiple R″ are the same or different, and multiple -X2-R′ are the same or different.

[0024]

[0025] In formula (III-1), Y1, Y2 and Y3 independently represent hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, methylalkyl ethers with 1 to 20 carbon atoms, methylaryl ethers with 6 to 25 carbon atoms, methylalkenyl ethers with 2 to 4 carbon atoms, alkylphenol groups, aromatic phenol groups, or alkenyl groups with 1 to 20 carbon atoms; a, b and c independently represent 0 to 30, and the sum of a, b and c is 1 to 90; "*" represents the position of the bond.

[0026] According to some embodiments of the present invention, the aforementioned Y1, Y2 and Y3 are not the same as each other.

[0027] According to some embodiments of the present invention, prior to the aforementioned ring-opening reaction, this preparation method may selectively perform an addition reaction between the nuclear reactant and an epoxide compound having 2 or 3 carbon atoms.

[0028] According to another aspect of the present invention, a surfactant solution is provided. The surfactant solution comprises a multibranched surfactant, wherein the multibranched surfactant is prepared by the aforementioned method.

[0029] The multibranched surfactant, its preparation method, and the surfactant solution containing it, according to the present invention, can be easily formed through a ring-opening reaction to create a core structure and multiple branch structures bonded to the core structure. The branched structure of the multibranched surfactant effectively enhances its interfacial properties, and its terminal groups can be further used to modify resins, coatings, or polymer materials. Furthermore, by adjusting the number of bonds and the chain segment length of the branched structure, the resulting multibranched surfactant can be an amphiphilic molecule with an appropriate hydrophilic-lipophilic balance, thus exhibiting excellent interfacial properties. Detailed Implementation

[0030] The manufacture and use of embodiments of the present invention are discussed in detail below. However, it will be understood that these embodiments provide many applicable inventive concepts that can be implemented in a wide variety of specific contexts. The specific embodiments discussed are for illustrative purposes only and are not intended to limit the scope of the invention.

[0031] The multibranched surfactant of the present invention is prepared by performing a ring-opening reaction on the reaction mixture. Based on the structure of the multibranched surfactant, it can be divided into a core structure and multiple branched structures bonded to the core structure; therefore, the reaction mixture accordingly contains core reactants and branched reactants.

[0032] The nuclear reactants comprise polyols and polyamines having 2 to 20 carbon atoms. The polyols or polyamines may have the structure shown in formula (IV).

[0033]

[0034] In formula (IV), X1 represents a group having 2 to 20 carbon atoms, and X1 may or may not have a secondary amine; X 21 It represents a hydroxyl group (-OH) or a primary amine (-NH2); and n1 represents an integer not less than 2.

[0035] The aforementioned groups having 2 to 20 carbon atoms can be, for example, straight-chain alkyl, straight-chain alkenyl, branched alkyl, branched alkenyl, aromatic alkyl, cycloalkyl, cycloalkenyl, heterocyclic alkyl, heterocyclic alkenyl, the aforementioned groups having an ether group, and / or other suitable groups. It is understood that, in the aforementioned examples, when X1 has a secondary amine (-NH-), the secondary amine is bonded between two carbon atoms. If X1 has more than 20 carbon atoms, the excessively long carbon chain will lead to reduced compatibility as an antifoaming agent and difficulty in uniform dispersion. Preferably, X1 can represent a group having 2 to 10 carbon atoms. In formula (IV), X... 21 There are no particular restrictions on the position of the bond in X1, as long as X 21 It simply needs to be bonded to the carbon atoms of X1. Understandably, this is to facilitate the bonding of subsequent branching structures, X... 21 The bond position does not affect the bond formation in subsequent reactions. In other embodiments, in X1, and X... 21 Each carbon atom in the bond is bonded to only one X atom. 21 .

[0036] In equation (IV), it can be understood that X 21 The number of bonds is the value of n1, therefore, based on the structure of X1, X 21 The number of bonds (i.e., the range of n1 values) is predictable. For example, when X1 represents N carbons... C When X is a straight-chain alkyl group, based on the carbon chain structure of the straight-chain alkyl group, it can be understood that X...21 The number of bonds (i.e., the value of n1) can be greater than or equal to 2, and the maximum is (2N). C +2), which involves theoretical knowledge of synthetic reactions based on chain segment bonding angles, electronic distribution of bonds, reactivity of compounds, and steric hindrance of functional groups, which can be understood by those with general knowledge. 21 The range of n1 values ​​can be further determined based on the actual bonding configuration on the carbon chain. In some embodiments, n1 preferably represents an integer from 2 to 10, more preferably an integer from 2 to 8, and even more preferably an integer from 3 to 6. Secondly, when X1 has a secondary amine, the number of secondary amines can be n2, and the sum of n1 and n2 can be 2 to n, preferably 3 to 8. Wherein, n is greater than 2, preferably greater than 2 and less than or equal to 12, more preferably greater than 2 and less than or equal to 10, and even more preferably 3 to 8.

[0037] In some specific examples, nuclear reactants may include, but are not limited to, ethylene glycol, 2-propanediol, 1,3-propanediol, butanediol, pentanediol, neopentanediol, hexanediol, heptaethylenediol, octanediol, nonanediol, decanediol, glycerol, trimethylolpropane, pentaerythritol, bis(trimethylolpropane), dipentaerythritol, polyglycerol, sorbitol, alkyl glucoside, sugar alcohol, cyclic alcohol, ethylenediamine, propylenediamine, decanediamine, dodecyldiamine, tetradecyldiamine, dodecyl-1,3-propanediamine, tetradecyl-1,3-propanediamine, N-cocoyl-1,3-propanediamine, N-tallowyl-1,3-propanediamine, N-stearyl-1,3-propanediamine, N-oil N-1,3-propanediamine, diethylenetriamine, dipropylenetriamine, N-tallow-dipropylenetriamine, N,N-di(3-aminopropyl)dodecylamine, N-oleo-dipropylenetriamine, N,N-di(3-aminopropyl)tallow-amine, N′-(3-aminopropyl)-N,N-dimethyl-1,3-propanediamine, tripropylenetetramine, N-tallow-tripropylenetetramine, N-oleo-tripropylenetetramine, tetraethylenepentamine, monoisopropanolamine, diisopropanolamine, 2-(isopropylamino)ethanol, N-isopropyldiethanolamine, aminoethylethanolamine, other suitable polyols or polyamines, or any mixture of the above compounds.

[0038] Branched reactants may comprise compounds having an epoxy group. In some specific examples, branched reactants may have the structure shown in formula (II).

[0039]

[0040] In formula (II), Y represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkyl ether having 1 to 20 carbon atoms, an aromatic ether having 6 to 25 carbon atoms, an alkenyl ether having 2 to 4 carbon atoms, an alkylphenol group, an aromatic phenol group, or an olefin group having 1 to 20 carbon atoms.

[0041] In some specific examples, the branching reactants may include, but are not limited to, ethylene oxide, propylene oxide, butane oxide, 1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2-epoxytridecane, 1,2-epoxytetradecane, 1,2-epoxypentadecanane, 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane, phenylethylene oxide, tolylethylene oxide, styrylated phenylethylene oxide, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, pentyl glycidyl ether, and hexyl glycidyl ether. Glyceryl ether, heptyl glycidyl ether, octyl glycidyl ether, 2-ethylhexyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, 3-propylheptyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, heptadecanyl glycidyl ether, octadecyl glycidyl ether, phenyl glycidyl ether, tolyl glycidyl ether, styrylated phenyl glycidyl ether, benzyl glycidyl ether, tert-butyl phenyl glycidyl ether, cashew phenol glycidyl ether, allyl glycidyl ether, other suitable compounds having an epoxy group, or any mixture of the above compounds.

[0042] Based on the fact that 1 mole of the nuclear reactant has n hydroxyl and amino groups (including primary and secondary amines), the amount of branched reactant is preferably from n moles to 90n moles, more preferably from 2n moles to 40n moles, and even more preferably from 3n moles to 10n moles. When the amount of branched reactant is within the aforementioned range, the prepared multibranched surfactant can have at least two branched structures, and each branched structure has an appropriate molecular length, thus exhibiting good interfacial properties (such as: defoaming, emulsifying, dispersing, wetting, and acid and alkali resistance).

[0043] To enhance reactivity, the reaction mixture may selectively contain a catalyst. Those skilled in the art can employ appropriate catalyst types and adjust their amounts based on the reaction mechanisms of the nuclear reactants and branched reactants; therefore, details are omitted here. In some embodiments, the catalyst may comprise an acid catalyst or a base catalyst. In some specific examples, the catalyst may comprise, but is not limited to, triphenylphosphine, triethylamine, benzyltriethylammonium chloride, tetra-n-butylammonium bromide, sodium hydroxide, potassium hydroxide, aluminum chloride, boron trifluoride, tetraisopropoxytin, zinc perchlorate, other suitable catalyst materials, or any mixture thereof.

[0044] During the reaction, the epoxy groups of the branched reactants can undergo ring-opening reactions and bond with the hydroxyl or amino groups of the core reactant. The branched reactants can also bond with each other, thereby forming the multibranched surfactant of the present invention as shown in formula (III). It is understood that the branched reactants after the ring-opening reaction are not limited to bonding with only the nitrogen atom of the terminal primary amine (-NH2) of the core reactant. When the core reactant contains a secondary amine (-NH-), the epoxy groups of the branched reactants can also bond with the nitrogen atom of the secondary amine.

[0045]

[0046] In formula (III), X1 represents an n-valent group with 2 to 20 carbon atoms, and X1 has n2 secondary amines, where n1 and n2 independently represent integers from 0 to n, and the sum of n1 and n2 is n; X2 represents -O-* or Furthermore, "*" represents the position of the bond with R; R″ is bonded to the nitrogen atom of the secondary amine of X1; R′ and R″ independently represent the structures shown in equation (III-1) below; n represents an integer not less than 2. When n1 and n2 independently represent integers not less than 2, multiple R″ are the same or different, and multiple -X2-R′ are the same or different.

[0047]

[0048] In formula (III-1), Y1, Y2, and Y3 independently represent hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, methylalkyl ethers with 1 to 20 carbon atoms, methylaryl ethers with 6 to 25 carbon atoms, methylalkenyl ethers with 2 to 4 carbon atoms, alkylphenol groups, aromatic phenol groups, or alkenyl groups with 1 to 20 carbon atoms, wherein the methyl groups of methylalkyl ethers, methylaryl ethers, and methylalkenyl ethers are all bonded between the carbon chains of the ether group and the ethoxy group; a, b, and c independently represent 0 to 30, and the sum of a, b, and c is 1 to 90; "*" represents the position of the bond.

[0049] It is understandable that the value of n for the n-valent group represented by X1 is defined by the structure of the nuclear reactant shown in formula (IV). The relevant description has been detailed above, and therefore will not be repeated here.

[0050] In some embodiments, Y1, Y2, and Y3 are not the same as each other. When Y1, Y2, and Y3 are not the same as each other, these different branched groups can impart better interfacial properties to the prepared multi-branched surfactant. Preferably, Y1, Y2, and Y3 can independently represent hydrogen atoms, methyl, ethyl, propyl, butyl, dodecyl, tetradecyl, methyl ethyl ether, methyl propyl ether, methyl butyl ether, methyl 2-ethylhexyl ether, methyl dodecyl ether, methyl tetradecyl ether, methyl phenyl ether, methyl tolyl ether, methyl styrene phenyl ether, methyl benzyl ether, methyl tert-butyl phenyl ether, methyl cashew ether, or methyl allyl ether, etc. In some embodiments, at least one of Y1, Y2, and Y3 is not a hydrogen atom, methyl, or ethyl. When at least one of Y1, Y2, and Y3 is not a hydrogen atom, methyl, or ethyl, the prepared multi-branched surfactant can have better interfacial properties. The sum of a, b, and c can be from 2 to 40, and more preferably from 3 to 10. When the sum of a, b, and c falls within the aforementioned range, each branch structure of the multibranched surfactant can have an appropriate molecular length, thereby enabling the multibranched surfactant to possess superior interfacial properties. In some embodiments, at least two of a, b, and c are not 0, and the sum of a, b, and c can be from 2 to 90, wherein the sum of a, b, and c is preferably from 2 to 40, and more preferably from 3 to 10. In these embodiments, Y1, Y2, and Y3 can be the same or different from each other. In some embodiments, in the prepared multibranched surfactant, the molecular structure of each branch structure can be the same or different from each other, and the molecular length of each branch structure can also be the same or different from each other. It is understood that when the molecular structure of each branch structure of the multibranched surfactant is the same, the multibranched surfactant can be prepared by a one-step reaction (i.e., a ring-opening reaction). In some embodiments, the terminal groups of the branched structures of the multi-branched surfactant of the present invention are preferably not ethylene oxide segments, in order to have better defoaming properties. Wherein, if each branched structure has a different segment structure, the defoaming properties of the multi-branched surfactant increase as the number of branched structures with terminal ethylene oxide segments decreases.

[0051] In some embodiments, n is preferably greater than 2 and less than or equal to 12, more preferably greater than 2 and less than or equal to 10, and even more preferably 3 to 8. When n is in the aforementioned range, the core structure of the multibranched surfactant can have an appropriate valence number for the branching structure to bond, thereby improving the interfacial properties of the multibranched surfactant.

[0052] Prior to the aforementioned ring-opening reaction, the core reactant of formula (IV) (i.e., a polyol or polyamine compound) may selectively undergo an addition reaction with an epoxy compound having 2 or 3 carbon atoms (e.g., ethylene oxide and / or propylene oxide) to form a modified core reactant. This modified core reactant can then be further reacted with a branched compound via a ring-opening reaction to form the multibranched surfactant of the present invention as shown in formula (III). In some embodiments, based on the number of hydroxyl or amino groups per mole of the core reactant being n, the amount of the epoxy compound having 2 or 3 carbon atoms is preferably 2 to 3n moles, and more preferably n to 3n moles. In some embodiments, the amount of the epoxy compound having 2 or 3 carbon atoms may be the same as or different from the amount of the branched compound. During the addition reaction, the epoxy groups of the epoxy compound having 2 or 3 carbon atoms react with the hydroxyl or amino groups of the core reactant via a ring-opening reaction to form the modified core reactant. By using extended segments formed from epoxides with 2 or 3 carbon atoms, branched reactants can more easily bond to the ends of these extended segments, resulting in multi-branched surfactants with superior interfacial properties. In some embodiments, during the addition reaction, the 2 or 3 carbon-carbon epoxide reacts with some of the hydroxyl or amino groups of the core reactant, resulting in each branch of the multi-branched surfactant having a different segment structure, thereby enhancing its interfacial properties.

[0053] In some specific examples, the branched surfactants of the present invention may be, for example, but not limited to, comb-shaped compounds, star-shaped compounds, dendrimer compounds, and / or other suitable types of compounds. Preferably, the branched surfactants may be star-shaped compounds or dendrimer compounds.

[0054] The multi-branched surfactant prepared by this invention possesses lipophilic groups ranging from lower to higher alcohols, and its hydrophilic-lipophilic balance can be adjusted through alkyl carbon chains or epoxides with 2 or 3 carbon atoms, resulting in excellent interfacial properties such as emulsification, dispersibility, solubilization, wetting, and lubrication. Secondly, the multi-branched surfactant of this invention has multiple branched structures, thus exhibiting better defoaming properties, acid and alkali resistance, compatibility, cold resistance, and low-temperature fluidity compared to general non-silicone surfactants such as polyethers, alcohols, or fatty acid esters. Furthermore, its highly branched structure helps suppress precipitation defects caused by siloxane bonds in traditional defoamers. In addition, the amphiphilic structure and terminal functional groups of the branched structure of the multi-branched surfactant of this invention can be further modified, making it suitable for modifying resin materials, coatings, and polymer materials.

[0055] In some applications, the branched surfactant of the present invention can be mixed with other components (such as different surfactants and / or solvents) to form a surfactant solution.

[0056] The following examples illustrate the application of the present invention, but are not intended to limit the invention. Any person skilled in the art can make various modifications and refinements without departing from the spirit and scope of the invention.

[0057] Preparation of multibranched surfactants

[0058] Example 1

[0059] One mole of trimethylolpropane was added to the reaction flask and heated to 50°C. Then, six moles of butyl glycidyl ether and a catalytic amount of tetra-n-butylammonium bromide were added to the reaction flask and heated to 100°C to carry out the ring-opening reaction. After 8 hours of reaction, the multibranched surfactant of Example 1, as shown in formula (V-1), was obtained.

[0060]

[0061] Example 2

[0062] Add 1 mole of trimethylolpropane to the reaction flask and heat to 50°C. Then, add 15 moles of butyl glycidyl ether and a catalytic amount of benzyltriethylammonium chloride to the reaction flask to carry out the ring-opening reaction at 100°C. After 8 hours, the intermediate product of Example 2 can be obtained.

[0063] Then, the above intermediate product, 6 moles of ethylene oxide and a catalytic amount of potassium hydroxide are added to a high-temperature and high-pressure reactor and heated to 150°C to 160°C to carry out a ring-opening reaction, thereby obtaining the multibranched surfactant of Example 2 as shown in formula (V-2).

[0064]

[0065] Example 3

[0066] One mole of pentaerythritol was added to a high-temperature, high-pressure reactor, along with four moles of ethylene oxide and a catalytic amount of potassium hydroxide, to carry out an addition reaction at 150°C to 160°C, forming a modified nucleus reactant. Next, eight moles of butyl glycidyl ether were added to the reactor, and the mixture was heated to 120°C to carry out a ring-opening reaction. After 5 hours, the multibranched surfactant of Example 3, as shown in formula (V-3), was obtained.

[0067]

[0068] Example 4

[0069] One mole of pentaerythritol was added to a high-temperature, high-pressure reactor, along with four moles of branched reactants (containing dodecyl glycidyl ether and tetradecyl glycidyl ether) and a catalytic amount of triphenylphosphine. The reactor was then heated to 120°C to initiate a ring-opening reaction. After 8 hours, the multibranched surfactant of Example 4, as shown in formula (V-4), was obtained. Here, R″′ represents dodecyl or tetradecyl.

[0070]

[0071] Example 5

[0072] Add 1 mole of ethylenediamine to a high-temperature and high-pressure reactor, along with 8 moles of ethylene oxide, 20 moles of propylene oxide, and a catalytic amount of potassium hydroxide, to carry out an addition reaction at 130°C to 140°C to form a modified nuclear reactant.

[0073] Then, the modified nuclear reactant and 10 moles of butyl glycidyl ether were added to the reactor and heated to 120°C to carry out the ring-opening reaction. After 4 hours, the multibranched surfactant of Example 5, as shown in formula (V-5), was obtained.

[0074]

[0075] Example 6

[0076] Add 1 mole of sorbitol to a high-temperature and high-pressure reactor, along with 25 moles of ethylene oxide and a catalytic amount of potassium hydroxide, to carry out an addition reaction at 150°C to 160°C to form a modified nuclear reactant.

[0077] Then, the modified nuclear reactant, 18 moles of butyl glycidyl ether and boron trifluoride were added to the reactor and heated to 70°C to 80°C to carry out the ring-opening reaction. After 1 to 2 hours, the multibranched surfactant of Example 6, as shown in formula (V-6), was obtained.

[0078]

[0079] Evaluation method - Defoaming property

[0080] An aqueous solution of octyl phenol ethoxylate (Triton X-100) was prepared, and based on a 100 wt% weight of this aqueous solution, 1 wt% of the surfactant from the examples or comparative examples was added. The defoaming properties of the surfactant were then evaluated at 25°C using the Rose-Miles method, and the evaluation results are shown in Table 1. Specifically, the surfactant in Comparative Example 1 was a commercial product manufactured by Chuji Synthetic, model TL-260; the surfactant in Comparative Example 2 was a commercial product manufactured by Chuji Synthetic, model PE81; and the surfactant in Comparative Example 3 was a commercial product manufactured by Chuji Synthetic, model GL-F50.

[0081] Table 1

[0082]

[0083] As shown in Table 1, the branched surfactant of the present invention has good defoaming properties. However, compared to Examples 1 and 3 to 6 (where the terminal structures of the branched structures contain butyl ether, dodecyl ether, or tetradecyl ether), the branched surfactant of Example 2 has relatively low defoaming properties because the terminal structures of its branched structures are all ethylene oxide segments. Nevertheless, it is understood that Example 2 can still effectively eliminate foam compared to the comparative examples.

[0084] Furthermore, while Comparative Example 3 effectively eliminated foam, its defoaming speed was relatively slow, and its defoaming performance was worse than that of Examples 1 to 6. Therefore, the surfactant in Comparative Example 3 still exhibits the shortcomings of general non-silicone defoamers and cannot meet the application requirements.

[0085] Accordingly, the multibranched surfactant of the present invention and the surfactant solution containing it can possess excellent interfacial properties through a specific core structure and multiple branched structures, and the terminal groups of the branched structures can be used to further modify resins, coatings, or polymer materials. Furthermore, the multibranched surfactant of the present invention can be easily prepared through a ring-opening reaction, effectively reducing process costs.

[0086] Although the present invention has been disclosed above by way of embodiments, it is not intended to limit the present invention. Anyone with ordinary knowledge in the art to which this invention pertains may make various modifications and refinements without departing from the spirit and scope of the present invention. Therefore, the scope of protection of the present invention shall be determined by the appended claims.

Claims

1. A multi-branched surfactant, characterized by, The multi-branched surfactant is used as an antifoaming agent, and has a structure shown in the following formula (I): In the formula (I), X represents a polyol group or a polyamine group having a carbon number of 2 to 20, R represents a structure shown in the following formula (I-1), and q represents an integer not less than 2. In the formula (I-1), R1 and R2 independently represent a hydrogen atom, an alkyl group having a carbon number of 1 to 20, a meroalkyl alkyl ether having a carbon number of 1 to 20, a meroalkyl aromatic ether having a carbon number of 6 to 25, a meroalkyl alkenyl ether having a carbon number of 2 to 4, an alkyl phenol group, an aromatic phenol group, or an alkenyl group having a carbon number of 1 to 20, R3 independently represents an alkyl group having a carbon number of 1 to 20, a meroalkyl alkyl ether having a carbon number of 1 to 20, a meroalkyl aromatic ether having a carbon number of 6 to 25, a meroalkyl alkenyl ether having a carbon number of 2 to 4, an alkyl phenol group, an aromatic phenol group, or an alkenyl group having a carbon number of 1 to 20, R1, R2 and R3 are not the same as each other; the sum of x, y and z is 3 to 10; and "*" represents a bonding position of the formula (I-1) and an oxygen atom of the polyol group or a nitrogen atom of the polyamine group.

2. The multi-branched surfactant of claim 1, wherein, The polyol group or the polyamine group has 2 to 10 hydroxyl groups and / or amine groups, and q represents an integer of 2 to 10.

3. The multi-branched surfactant of claim 2, wherein, The amine group includes a primary amine and / or a secondary amine.

4. A method of making a multi-branched surfactant, comprising: The manufacturing method includes: The multi-branched surfactant is used as an antifoaming agent, and has a structure shown in the following formula (I): The multi-branched surfactant is used as an antifoaming agent, and has a structure shown in the following formula (I): In the formula (I-1), R1 and R2 independently represent a hydrogen atom, an alkyl group having a carbon number of 1 to 20, a meroalkyl alkyl ether having a carbon number of 1 to 20, a meroalkyl aromatic ether having a carbon number of 6 to 25, a meroalkyl alkenyl ether having a carbon number of 2 to 4, an alkyl phenol group, an aromatic phenol group, or an alkenyl group having a carbon number of 1 to 20, R3 independently represents an alkyl group having a carbon number of 1 to 20, a meroalkyl alkyl ether having a carbon number of 1 to 20, a meroalkyl aromatic ether having a carbon number of 6 to 25, a meroalkyl alkenyl ether having a carbon number of 2 to 4, an alkyl phenol group, an aromatic phenol group, or an alkenyl group having a carbon number of 1 to 20, R1, R2 and R3 are not the same as each other; the sum of x, y and z is 3 to 10; and "*" represents a bonding position. Based on 1 mole of the core reactant, the amount of the branch reactant is at least 2 moles. The compound having one epoxy group has a structure shown in the following formula (II): In formula (III), X1represents an n-valent group having a carbon number of 2 to 20, and X1has n2secondary amines, wherein n1and n2independently represent an integer of 0 to n, and the sum of n1and n2is n; X2represents -O- or and "*" represents a position bonded to R'; R" is bonded to the nitrogen atom of each secondary amine of X1; R' and R" independently represent a structure shown in formula (III-1) below; n represents an integer of not less than 2, and when n1and n2independently represent an integer of not less than 2, a plurality of R" are the same or different, and a plurality of -X2-R' are the same or different: In the formula (II), Y represents a hydrogen atom, an alkyl group having a carbon number of 1 to 20, a meroalkyl alkyl ether having a carbon number of 1 to 20, a meroalkyl aromatic ether having a carbon number of 6 to 25, a meroalkyl alkenyl ether having a carbon number of 2 to 4, an alkyl phenol group, an aromatic phenol group, or an alkenyl group having a carbon number of 1 to 20.

5. The method of claim 4, wherein the polybranched surfactant is produced by the reaction of a polyamine with a polyepoxide. Before the ring-opening reaction is performed, the manufacturing method further includes:

6. The method of claim 4, wherein the polybranched surfactant is produced by the reaction of a polyamine with a diacyl halide. An addition reaction is performed on the core reactant and an epoxy compound having a carbon number of 2 or 3. ​ 7. The method of claim 4, wherein the polybranched surfactant is produced by the reaction of a polyol with a fatty acid in the presence of a catalyst. ​ ​

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