CN111203150B - Nonionic surfactant and preparation method thereof - Google Patents
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- CN111203150B CN111203150B CN202010007143.0A CN202010007143A CN111203150B CN 111203150 B CN111203150 B CN 111203150B CN 202010007143 A CN202010007143 A CN 202010007143A CN 111203150 B CN111203150 B CN 111203150B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3318—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group heterocyclic
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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Abstract
The invention relates to a novel nonionic surfactant and a preparation method thereof. The nonionic surfactant has the following general structure (I):
(1) in the formula (1), R 1 Is one or more selected from saturated or unsaturated hydrocarbon chains with carbon chain length of 4-18 carbon atoms; r 2 O is one or more selected from oxyalkylene groups having 2 to 4 carbon atoms; m represents an average molar number of addition of the oxyalkylene group and is an integer or fraction of 3 to 40; n represents an average addition mole number of styrene oxide and is an integer or fraction of more than 0 and not more than 5. The invention also relates to a preparation method of the nonionic surfactant. By introducing a styrene oxide structure into the fatty alcohol alkylate, the novel nonionic surfactant provided by the invention improves the application performance, maintains strong decontamination, oil removal and emulsification capabilities, improves the low-temperature fluidity and reduces the foam.
Description
Technical Field
The invention relates to the technical field of surfactants, and in particular relates to a surfactant and a preparation method thereof.
Background
The application of the surfactant is very wide, and the surfactant is deeply applied to various civil and industrial fields. The surfactant includes ionic surfactants, nonionic surfactants and the like. Wherein the nonionic surfactant does not ionize in water and is an amphiphilic structure molecule taking hydroxyl or ether bond as hydrophilic group. The nonionic surfactant has the characteristic of non-ionization in water, so that the nonionic surfactant is more excellent than the ionic surfactant in certain aspects, for example, the nonionic surfactant has better solubility in water and organic solvents, has high stability in a solution, is not easily influenced by strong electrolyte inorganic salts, acids and alkalis, and the like. Because the surfactant has good compatibility with other types of surfactants, the surfactant can be mixed with other surfactants for compounding. The nonionic surfactant has the characteristics of good hard water resistance and low foaming property, so that the nonionic surfactant is suitable for being used as a special detergent. In addition, it has important applications in many fields because it has various properties of dispersion, emulsification, foaming, wetting and solubilization.
The fatty alcohol ether is widely used non-ionic surfactant, and has the characteristics of wide raw material source, good biodegradability, strong emulsifying capacity and the like. However, the main problems of the nonionic surfactants are that the comprehensive performance is not excellent enough, low foam, strong emulsification, good low-temperature fluidity and the like cannot be considered, and multiple products are required to be compounded and used in the actual use process.
Therefore, there is still a need in the art for a nonionic surfactant that can improve low temperature fluidity, reduce foam, and the like, while maintaining high detergency, oil removal, and emulsification.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide the nonionic surfactant based on the fatty alcohol polyoxyalkyl ether, so as to overcome the limitations of some applications of the current nonionic surfactant products and simultaneously improve the comprehensive properties of the nonionic surfactant products, such as foam reduction, low-temperature fluidity improvement, pour point reduction, strong emulsifying capacity maintenance and the like.
The above purpose is realized by the following technical scheme:
in a first aspect, there is provided a nonionic surfactant having the following general structure (1):
in the formula (1), R 1 Can be one selected from saturated or unsaturated hydrocarbon chains with carbon chain length of 4-18 carbon atoms; r 2 O may be one selected from oxyalkylene groups having 2 to 4 carbon atoms; m represents an average molar number of addition of the oxyalkylene group and is an integer or fraction of 3 to 40; n represents an average addition mole number of styrene oxide and is an integer or fraction of more than 0 and not more than 5.
In the technical scheme, as the styrene oxide structure is introduced into the fatty alcohol alkylate, the application performance of the surfactant is improved, so that the low-temperature fluidity of the surfactant is improved and the foam is reduced while the strong decontamination, oil removal and emulsification capabilities are maintained.
The nonionic surfactant according to the first aspect, wherein R 1 May be one selected from C12-14 alkyl, isomeric C13 alkyl, C16-18 alkyl and isooctyl.
The nonionic surfactant according to the first aspect, wherein R 2 O may be one selected from an oxyethylene group, an oxypropylene group, and an oxybutylene group, and is preferably an oxyethylene group or an oxypropylene group.
The nonionic surfactant according to the first aspect, wherein m is an integer or fraction of 3 to 30, 3 to 20, 3 to 15, 3 to 9, 5 to 30, 5 to 20, 5 to 15, 5 to 9, 9 to 30, 9 to 20, 9 to 15, preferably 5, 9 or 40.
The nonionic surfactant according to the first aspect, wherein n is an integer or fraction of 0.1 to 5, 0.5 to 4, 0.5 to 3, 0.5 to 2, 0.5 to 1, preferably 0.5, 0.8 or 1.
In a second aspect, there is provided a process for the preparation of a nonionic surfactant according to the first aspect, the process comprising the steps of:
taking fatty alcohol ether as an initiator, carrying out quantitative ring-opening addition reaction with styrene oxide for 3-5h at the reaction temperature of 40-120 ℃ under the action of an alkaline catalyst, and then adding acid for neutralization to obtain a nonionic surfactant fatty alcohol polyoxyalkyl polyoxyethyl ether;
wherein the fatty alcohol ether has the general formula:
wherein R is 1 Can be one selected from saturated or unsaturated hydrocarbon chains with carbon chain length of 4-18 carbon atoms; r 2 O may be one selected from oxyalkylene groups having 2 to 4 carbon atoms; m represents an average molar number of addition of the oxyalkylene group and is an integer or a fraction of 3 to 40.
By this method, the nonionic surfactant can be obtained. The method has the advantages of simple steps, easily obtained raw materials, mild reaction conditions, short reaction time and the like.
The process according to the second aspect, wherein the basic catalyst is selected from one or more of NaOH, KOH, NaOMe.
The alkaline condition is favorable for opening the ring of the epoxy compound (especially cyclic ether), and especially strong alkaline conditions such as sodium hydroxide, potassium hydroxide and the like. Under the catalytic action of the alkali, the fatty alcohol is dissociated into alcohol anions to attack the epoxy group of the epoxy compound to open the ring, so that the alcohol ether compound is produced.
The process according to the second aspect, the molar ratio of styrene oxide to fatty alcohol ether is from 0.5 to 5:1, preferably 1: 1.
The process according to the second aspect, wherein the reaction temperature is preferably 80 ℃.
At this temperature, the rate of the ring-opening reaction increases due to the ion-pair mechanism of action, which contributes to shortening the reaction time.
Compared with the prior art, the invention has the following advantages:
1. according to the invention, the styrene oxide structure is introduced into the fatty alcohol alkylate, so that the application performance of the fatty alcohol alkylate is improved, the low-temperature fluidity is improved and the foam is reduced while the strong decontamination, oil removal and emulsification capabilities are maintained;
2. the preparation method provided by the invention is simple and convenient, has various forms and wide application range;
3. the nonionic surfactant prepared by the invention has the characteristics of special characteristics and wide application. The nonionic surfactant has excellent oil removal, decontamination, emulsification and low foaming performances and good low-temperature fluidity, and can be widely applied to a plurality of fields including but not limited to textile, daily chemical and pesticide industries.
Detailed Description
Some specific embodiments of the present invention will be described below with reference to examples. Those of ordinary skill in the art will appreciate that these examples are provided merely to illustrate how the invention can be practiced and are not intended to limit the scope of the invention in any way.
Fatty alcohol ethers are widely applied nonionic surfactants at present, have the characteristics of wide raw material sources, good biodegradability, strong emulsifying capacity and the like, but have poor comprehensive performance, cannot give consideration to low foam, strong emulsification, good low-temperature fluidity and the like, and need to be compounded with various products in the actual use process. The inventors of the present application therefore intend to improve this. Through extensive practice, the inventors of the present application found that by introducing a styrene oxide structure into a fatty alcohol alkylate, the oil removal, stain removal, emulsification, low foaming properties, etc. of the resulting nonionic surfactant can be improved while having good low temperature fluidity. The present invention has been completed on the basis of this finding.
The nonionic surface active according to the present invention can be conveniently prepared by the reaction of the following formula (2):
in the formula (2), R 1 Is a saturated or unsaturated hydrocarbon chain, the length of the carbon chain is 4-18 carbon atoms, and one or more of the carbon chains can be used; r 2 O represents oxyalkylene group having 2 to 4 carbon atoms, and may be one or more; m represents an average molar number of addition of the oxyalkylene group and is an integer or fraction of 3 to 40; n represents an average addition mole number of styrene oxide and is an integer or fraction of more than 0 and not more than 5.
The nonionic surfactant of the present invention will be described and illustrated in more detail with reference to examples. Those of ordinary skill in the art will appreciate that these examples are provided for illustrative purposes only, and that those of ordinary skill in the art will better understand how to implement the present invention and will not set forth any limitations on the scope of the present invention.
Examples
Example 1
This example prepares a nonionic surfactant having the following structural formula (3):
the preparation method of the nonionic surfactant comprises the following steps:
1. stock preparation
C12-14 alcohol polyoxyethylene ether AEO-9 (mixed fatty alcohol available on the market); styrene oxide (commercially available); catalyst: sodium hydroxide (commercially available).
2. Addition of catalyst
After 100 g of C12-14 alcohol polyoxyethylene ether AEO-9 is added into a reaction kettle at room temperature, 0.3 g of sodium hydride solid is added into the reaction kettle for nitrogen displacement, and then the reaction kettle is vacuumized to be below-0.09 MPa. Heating the reaction kettle to 100 ℃, and treating for 1h to obtain dehydrated C12-14 alcohol polyoxyethylene ether AEO-9.
3. Addition reaction
And (3) introducing 20 g of styrene oxide into the dehydrated C12-14 alcohol polyoxyethylene ether AEO-9, and performing addition reaction for 3h at the temperature of 100 ℃ to obtain an addition product. Finally, 0.2 g of acetic acid neutralization catalyst was added to the reaction vessel to obtain 120.3 g of C12-14 alcohol polyoxyalkyl ether.
4. Performance testing
The C12-14 alcohol polyoxyalkyl ether prepared according to example 1 was tested for emulsifying power, pour point, and foam properties as follows, using commercially available C12-14 alcohol polyoxyethylene ether AEO-9 as control 1.
And (3) testing the emulsifying power: preparing 1g/L aqueous solution of a surfactant to be detected, putting 40ml of the liquid to be detected and 5# white oil into a 100ml high-leg beaker respectively, standing in a 100ml measuring cylinder with a plug after the average value is 60s at the rotating speed of 1000r/min of a homogenizer, and recording the time required by 10ml of water phase separated from the lower layer. The longer the time required for delamination, the greater the emulsifying power of the test specimen.
Pour point test: the method is carried out according to the reference GB/T3535-2006. Specifically, the sample was heated and then cooled at the cooling rate specified by the national standard, and the fluidity of the sample was observed at every 3 ℃ and the lowest temperature at which the sample was observed to be flowable was recorded as the pour point. The lower the pour point, the better the cold flow, the more convenient it is to use.
And (3) foam testing: preparing 1g/L aqueous solution of a surfactant to be detected, putting 40ml of the solution to be detected in a 100ml measuring cylinder, shaking up and down for 10 times, and recording the height of upper-layer foam (recording the number of milliliters of foam, ml), wherein the larger the numerical value, the higher the foam.
The emulsification, pour point, foam test results are listed in table 1.
Example 2
This example prepares a nonionic surfactant having the following structural formula (4):
the preparation method of the nonionic surfactant comprises the following steps:
1. stock preparation
Isomeric C13 alcohol polyoxyethylene ethers 1315 (commercially available); styrene oxide (commercially available); catalyst: potassium hydroxide (purchased in the market, and according with the chemical industry Standard of the people's republic of China GB/T1919-2000).
2. Addition of catalyst
100 g of isomeric C13 alcohol polyoxyethylene ether 1315 is added into a reaction kettle at room temperature, then 0.4 g of 50 percent KOH aqueous solution is added into the reaction kettle for nitrogen replacement, and then the reaction kettle is vacuumized to be below-0.09 MPa. Heating the reaction kettle to 100 ℃, and treating for 1h to obtain dehydrated isomeric C13 alcohol polyoxyethylene ether 1315.
3. Addition reaction
7 g of styrene oxide is pumped into the dehydrated isomeric C13 alcohol polyoxyethylene ether 1315, and the addition reaction is carried out for 1.5h at the temperature of 80 ℃ to obtain an addition product. Finally, 0.2 g of acetic acid as a catalyst for neutralization was added to the reaction vessel to obtain 107.4 g of isomeric tridecanol polyoxyalkyl ether.
4. Performance testing
The isomeric tridecanol polyoxyalkyl ethers prepared in accordance with example 2 were tested for emulsifying power, pour point, and foam properties as follows, using the commercially available isomeric C13 alcohol polyoxyethylene ether 1315 as control sample 2.
And (3) testing emulsifying power: preparing 1g/L aqueous solution of a surfactant to be detected, putting 40ml of the liquid to be detected and 5# white oil into a 100ml high-leg beaker respectively, standing in a 100ml measuring cylinder with a plug after the average value is 60s at the rotating speed of 1000r/min of a homogenizer, and recording the time required by 10ml of water phase separated from the lower layer. The longer the time required for delamination, the greater the emulsifying power of the test specimen.
Pour point testing: the method is carried out according to the reference GB/T3535-2006. Specifically, after the sample was heated, it was cooled at a predetermined cooling rate, and the fluidity of the sample was observed at every 3 ℃ and the lowest temperature at which the sample was observed to be able to flow was recorded as the pour point. The lower the pour point, the better the cold flow, the more convenient it is to use.
And (3) foam testing: preparing 1g/L aqueous solution of a surfactant to be detected, putting 40ml of the solution to be detected in a 100ml measuring cylinder, shaking up and down for 10 times, and recording the height of upper-layer foam (recording the number of milliliters of foam, ml), wherein the larger the numerical value, the higher the foam.
The emulsification, pour point, foam results are listed in table 1.
Example 3
This example prepares a nonionic surfactant having the following structural formula (5):
the preparation method of the nonionic surfactant comprises the following steps:
1. stock preparation
C16-18 alcohol polyoxyethylene 6840 (a commercially available mixed alcohol ether); styrene oxide (commercially available); catalyst: NaOMe alcohol solution (commercially available, in accordance with the chemical industry Standard of the people's republic of China HG/T2561-94).
2. Addition of catalyst
100 g of C16-18 alcohol polyoxyethylene ether 6840 is added into a reaction kettle at room temperature, 0.2 g of NaOMe alcohol solution is added into the reaction kettle for nitrogen replacement, and then the reaction kettle is vacuumized to be below-0.09 MPa. Heating the reaction kettle to 100 ℃, and treating for 1h to obtain dehydrated C16-18 alcohol polyoxyethylene ether 6840.
3. Addition reaction
6.5 g of styrene oxide is introduced into the dehydrated C16-18 alcohol polyoxyethylene ether 6840, and an addition reaction is carried out for 1.5h at the temperature of 100 ℃ to obtain an addition product. Finally, 0.1g of acetic acid neutralization catalyst was added to the reaction vessel to obtain 106.7 g of C16-18 alcohol polyoxyalkyl ether.
4. Performance testing
The C16-18 alcohol polyoxyalkyl ether prepared according to example 3 was tested for emulsifying power, pour point, and foam properties as follows, using the commercially available C16-18 alcohol polyoxyethylene ether 6840 as control sample 3.
And (3) testing the emulsifying power: preparing 1g/L aqueous solution of a surfactant to be detected, putting 40ml of the liquid to be detected and 5# white oil into a 100ml high-leg beaker respectively, standing in a 100ml measuring cylinder with a plug after the average value is 60s at the rotating speed of 1000r/min of a homogenizer, and recording the time required by 10ml of water phase separated from the lower layer. The longer the time required for delamination, the greater the emulsifying power of the test specimen. Pour point test: refer to national standard GB/T3535-2006. Specifically, the sample was heated and then cooled at a predetermined cooling rate, and the fluidity of the sample was observed at every 3 ℃ and the lowest temperature at which the sample was observed to be able to flow was recorded as the pour point. Lower pour points represent better low temperature flow and are more convenient to use.
And (3) foam testing: preparing 1g/L aqueous solution of a surfactant to be detected, putting 40ml of the solution to be detected in a 100ml measuring cylinder, shaking up and down for 10 times, and recording the height of upper-layer foam (recording the number of milliliters of foam, ml), wherein the larger the numerical value, the higher the foam.
The emulsification, pour point, foam test results are listed in table 1.
Example 4
This example prepares a nonionic surfactant having the following structural formula (6):
the preparation method of the nonionic surfactant comprises the following steps:
1. stock preparation
Isooctanol polyoxyalkyl ether EH9 (commercially available as a finished mixture); styrene oxide (commercially available); catalyst: potassium hydroxide (commercially available, chemical industry Standard of the people's republic of China GB/T1919-2000).
2. Addition of catalyst
100 g of isooctanol polyoxy alkyl ether EH9 was added to a reaction vessel at room temperature, 0.2 g of KOH solid was added to the reaction vessel, nitrogen gas was substituted, and the reaction vessel was evacuated to-0.09 MPa or less. Heating the reaction kettle to 100 ℃ after starting heating, and obtaining dehydrated isooctanol polyoxyalkyl ether EH9 after 1h of treatment.
3. Addition reaction
And (3) introducing 12 g of styrene oxide into the dehydrated isooctanol polyoxyalkyl ether EH9, and carrying out addition reaction for 1.5h at the temperature of 80 ℃ to obtain an addition product. Finally, acetic acid is added into the reaction kettle for neutralization reaction, and 112.2 g of isooctanol polyoxy alkyl ether is prepared.
4. Performance test
The emulsifying ability, pour point and foam properties of the isooctanol polyoxyalkylene ether prepared according to example 4 were tested as follows, using commercially available isooctanol polyoxyalkylene ether EH9 as control sample 4.
The emulsifying power testing method comprises the following steps: preparing 1g/L aqueous solution of surfactant to be detected, putting 40ml of the liquid to be detected and 5# white oil into a 100ml high-leg beaker respectively, standing in a 100ml measuring cylinder with a plug after the average value is 60s at the rotation speed of 1000r/min of a homogenizer, and recording the time required by 10ml of water phase separated from the lower layer. The longer the time required for delamination, the greater the emulsifying power of the test specimen.
Pour point test: the method is carried out by referring to national standard GB/T3535-2006. Specifically, the sample was heated and then cooled at a predetermined cooling rate, and the fluidity of the sample was observed at 3 ℃ intervals, and the lowest temperature at which the sample could flow was observed was recorded as the pour point. The lower the pour point, the better the cold flow, the more convenient it is to use.
And (3) foam testing: preparing 1g/L aqueous solution of a surfactant to be detected, putting 40ml of the solution to be detected in a 100ml measuring cylinder, shaking up and down for 10 times, and recording the height of upper-layer foam (recording the number of milliliters of foam, ml), wherein the larger the numerical value, the higher the foam. The emulsification, pour point, foam results are shown in table 1.
Table 1 emulsification, pour point and foam of fatty alcohol polyoxyalkylene ether nonionic surfactants.
As can be seen from Table 1, the nonionic surfactant prepared by the invention has excellent comprehensive application performance in emulsification, foam, pour point and the like, and has great application potential.
The above description is intended to be illustrative of the present invention and should not be taken as limiting the invention, as the invention is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.
Claims (13)
1. A nonionic surfactant characterized by having the following general structure (1):
in the formula (1), R 1 Is one selected from C12-14 alkyl, C16-18 alkyl and isooctyl; r 2 O is one selected from oxyalkylene groups having 2 to 4 carbon atoms; m represents an average molar number of addition of the oxyalkylene group and is an integer or fraction of 3 to 40; n represents an average addition mole number of styrene oxide and is an integer or fraction of more than 0 and not more than 5.
2. The nonionic surfactant of claim 1, wherein R is 2 O is one selected from the group consisting of an oxyethylene group, an oxypropylene group, and an oxybutylene group.
3. The nonionic surfactant according to claim 1, wherein m is an integer or fraction of 3 to 30.
4. The nonionic surfactant according to claim 1, wherein m is an integer or a fraction of 5 to 30.
5. The nonionic surfactant according to claim 1, wherein m is an integer or fraction of 9 to 30.
6. The nonionic surfactant according to claim 1, wherein n is an integer or fraction of 0.1 to 5.
7. The nonionic surfactant according to claim 1, wherein n is an integer or fraction of 0.5 to 5.
8. The nonionic surfactant according to claim 1, wherein n is an integer or fraction of 0.5 to 1.
9. A process for preparing the nonionic surfactant according to any one of claims 1 to 8, characterized by comprising the steps of:
taking fatty alcohol ether as an initiator, carrying out quantitative ring-opening addition reaction with styrene oxide for 3-5h at the reaction temperature of 40-120 ℃ under the action of an alkaline catalyst, and then adding acid for neutralization to obtain a nonionic surfactant fatty alcohol polyoxyalkyl polyoxyethyl ether;
wherein the fatty alcohol ether has the general formula:
wherein R is 1 、R 2 O, m are each independently as claimed in any one of claims 1 to 8.
10. The method of claim 9, wherein the basic catalyst is selected from one or more of NaOH, KOH, NaOMe.
11. The method of claim 9, wherein the molar ratio of styrene oxide to fatty alcohol ether is 0.5-5: 1.
12. The method of claim 11, wherein the molar ratio of styrene oxide to fatty alcohol ether is 1: 1.
13. The process of claim 9, wherein the reaction temperature is 80 ℃.
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