CN113087894A - Cardanol polyoxyethylene ether, preparation method and application thereof - Google Patents
Cardanol polyoxyethylene ether, preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2603—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 from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—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 from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—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 from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2642—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 from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2648—Alkali metals or compounds thereof
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2642—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 from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2669—Non-metals or compounds thereof
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Abstract
The application relates to the technical field of polymer synthesis, and particularly discloses cardanol polyoxyethylene ether, and a preparation method and application thereof. The cardanol polyoxyethylene ether is prepared by taking cardanol and ethylene oxide as raw materials and performing sectional addition by using an organic base catalyst and an inorganic base catalyst; the preparation method comprises the following steps: s1, heating and pressurizing cardanol and ethylene oxide under the action of an organic base catalyst to perform polymerization reaction, curing after the reaction is finished, and vacuumizing to remove the organic base catalyst to obtain an intermediate product; and S2, continuously reacting the intermediate product with ethylene oxide, heating and pressurizing under the action of an inorganic base catalyst to perform polymerization reaction, curing after the reaction is finished, and adding acetic acid to neutralize to obtain the cardanol polyoxyethylene ether. The cardanol polyoxyethylene ether has the advantage of wide molecular weight distribution, so that the cardanol polyoxyethylene ether can be applied to industrial and civil cleaning agents, printing and dyeing industries, textile refining agents, coating additives and the like.
Description
Technical Field
The application relates to the technical field of polymer synthesis, in particular to cardanol polyoxyethylene ether, a preparation method and application thereof.
Background
With the technological progress and the industrial development, the production and the application of the surfactant are rapidly developed. The raw material sources of the surfactant production mainly comprise two major types of minerals and biomass, and at present, the surfactant product taking the minerals as the raw materials accounts for 75% of the total time of the surfactant in the world. However, in view of the availability of raw materials, the safety and compatibility of the environment and human body, the sustainability of industry development and the like, research and development of preparing low-toxicity, renewable and good-biodegradability surfactants by using biomass resources as raw materials are necessary, and the preparation method will become the leading direction of the industrial development of the surfactants in the future. Therefore, the research and development of the polyoxyethylene ether product taking the natural bio-based alkylphenol-cardanol as the initiator has profound significance when meeting the condition. Because it is derived from the fact that the nature is not living, and can be biologically degraded, it can protect the human ecological environment, and is a green chemical product.
In the related art, a single catalyst is mostly adopted for catalysis in preparation of cardanol polyoxyethylene ether, and a common catalyst comprises inorganic strong base and the like, but the single catalyst is used for catalytic reaction, so that the molecular weight distribution of the prepared cardanol polyoxyethylene ether is narrow, and the cardanol polyoxyethylene ether has more stable performance, but the application range of the cardanol polyoxyethylene ether is limited.
Disclosure of Invention
In order to improve the molecular weight distribution range of cardanol polyoxyethylene ether and further enable the cardanol polyoxyethylene ether to be widely applied to the fields of textile printing and dyeing, daily use clearness, metal cleaning and the like, the application provides cardanol polyoxyethylene ether, and a preparation method and application thereof.
In a first aspect, the application provides cardanol polyoxyethylene ether, which adopts the following technical scheme:
a cardanol polyoxyethylene ether has a structural formula as follows:
wherein, R is a hydrocarbon chain containing 15 carbon atoms, and can be respectively a saturated hydrocarbon chain or an unsaturated hydrocarbon chain containing monoene, diene and triene shown as the following:
C15H31，
C15H29，
C15H27，
C15H25，
n＝3-30；
the cardanol polyoxyethylene ether is prepared by taking cardanol and ethylene oxide as raw materials and performing sectional addition on the cardanol polyoxyethylene ether by using an organic base catalyst and an inorganic base catalyst.
By adopting the technical scheme, the cardanol is taken as a main raw material, is extracted and refined from natural cashew nut shell oil, and is a non-ionic surfactant with high biodegradability and environmental friendliness. According to the application, the cardanol polyoxyethylene ether is obtained by using the organic base catalyst and the inorganic base catalyst through segmented addition, so that the cardanol polyoxyethylene ether has wider molecular weight distribution compared with cardanol polyoxyethylene ether prepared in the related technology, the application range of the cardanol polyoxyethylene ether is expanded, and the cardanol polyoxyethylene ether can be applied to the fields of textile printing and dyeing, daily washing, metal washing and the like.
In a second aspect, the application provides a preparation method of cardanol polyoxyethylene ether, which adopts the following technical scheme: a preparation method of cardanol polyoxyethylene ether comprises the following steps:
s1, heating and pressurizing cardanol and ethylene oxide under the action of an organic base catalyst to perform polymerization reaction, curing after the reaction is finished, and vacuumizing to remove the organic base catalyst to obtain an intermediate product;
and S2, continuously reacting the intermediate product with ethylene oxide, heating and pressurizing under the action of an inorganic base catalyst to perform polymerization reaction, curing after the reaction is finished, and adding acetic acid to neutralize to obtain the cardanol polyoxyethylene ether.
By adopting the technical scheme, the preparation process of the cardanol polyoxyethylene ether is carried out in a segmented manner, so that the obtained cardanol polyoxyethylene ether has a wider molecular weight range, has better cleaning performance and low foaming property, has small smell, and is particularly suitable for industrial and civil cleaning agents. Because the molecular weight distribution is wider, the high-temperature washing resistance is also improved, and the method is suitable for a new washing and dyeing integrated process in the printing and dyeing industry. In addition, the cardanol polyoxyethylene ether prepared in the application has good wettability, and can be used as a textile refining agent, a coating additive, a wetting agent and an emulsifying agent in pesticide chemicals, an auxiliary emulsifying agent in emulsion polymerization and the like.
Preferably, the specific step of S1 is: adding cardanol into a reactor, introducing nitrogen, ensuring that the reaction is carried out in a nitrogen environment, stirring and heating to 90-100 ℃, dehydrating, adding an organic base catalyst, introducing ethylene oxide, setting the reaction temperature at 130-140 ℃, setting the reaction pressure at 0.1-0.3MPa, reacting for 2-4h, post-curing, and vacuumizing to remove the organic base catalyst to obtain an intermediate product.
By adopting the technical scheme, the cardanol and ethylene oxide are fully polymerized by regulating and controlling conditions such as reaction temperature, pressure, reaction time and the like of the first-step polymerization reaction to generate a stable intermediate product, and a foundation is laid for the second-step polymerization.
Preferably, the organic base catalyst is triethylamine, and the addition amount of the triethylamine is 0.2-0.4% of the addition amount of the cardanol.
By adopting the technical scheme, the added triethylamine is used as a stable catalyst, so that the polymerization rate can be accelerated, and the triethylamine does not participate in the polymerization reaction. Compared with an inorganic base catalyst, the triethylamine catalyst can be used for enabling the polymerization reaction to be stable and controllable, the loss rate of double bonds is reduced, the used triethylamine can be recycled, and the cost is saved.
Preferably, in S1, the molar ratio of cardanol to ethylene oxide is 1: (2-3).
By adopting the technical scheme, the molar ratio of cardanol to ethylene oxide is controlled within the range, so that cardanol and ethylene oxide are fully polymerized under the catalytic action of triethylamine, the generated intermediate product is relatively stable, and the second-step polymerization reaction is facilitated.
Preferably, the intermediate has the structural formula:
wherein, R is a hydrocarbon chain containing 15 carbon atoms, and can be respectively a saturated hydrocarbon chain or an unsaturated hydrocarbon chain containing monoene, diene and triene shown as the following:
C15H31，
C15H29，
C15H27，
C15H25，
n＝2-6。
by adopting the technical scheme, the intermediate product is the primarily polymerized cardanol polyoxyethylene ether, the molecular weight distribution is narrow, the rheological property is good, and the cardanol polyoxyethylene ether can continuously react with ethylene oxide under the conditions of adding a catalyst and controlling the reaction temperature and pressure, so that the molecular weight is further improved.
Preferably, the specific step of S2 is: adding an inorganic base catalyst into the reactor, introducing ethylene oxide, setting the reaction temperature at 130-140 ℃, setting the reaction pressure at 0.1-0.3MPa, reacting for 2-4h, curing, cooling, and adding acetic acid for neutralization to obtain the cardanol polyoxyethylene ether.
By adopting the technical scheme, synthesis of cardanol polyoxyethylene ether is promoted by regulating and controlling reaction temperature, pressure and time of the second-step polymerization reaction. After the reaction is finished, the catalyst component added in the reaction is removed by adding acetic acid, so that the purity of the prepared cardanol polyoxyethylene ether is improved.
Preferably, the inorganic base catalyst is potassium hydroxide, and the addition amount of the potassium hydroxide is 0.2-0.4% of the addition amount of the cardanol.
By adopting the technical scheme, the added potassium hydroxide is used as a catalyst, so that the polymerization reaction rate can be obviously accelerated, and meanwhile, the potassium hydroxide does not chemically react with each raw material component, so that the generation of the cardanol polyoxyethylene ether is promoted. Within the above-mentioned addition range, the potassium hydroxide can play the best catalytic role and promote the generation of cardanol polyoxyethylene ether.
Preferably, the molar ratio of the ethylene oxide added in S2 to the cashew phenol in S1 is (7-100): 1.
By adopting the technical scheme, the ethylene oxide in the range is added, so that the intermediate product can fully react with the ethylene oxide, and the prepared cardanol polyoxyethylene ether has a wider molecular weight and better high-temperature resistance and other properties.
In a third aspect, the application provides an application of cardanol polyoxyethylene ether, which adopts the following technical scheme:
the application of the cardanol polyoxyethylene ether is applied to industrial and civil cleaning agents, printing and dyeing industry, textile refining agents, coating additives, wetting agents in pesticide chemicals, emulsifying agents in pesticide chemicals and synthetic fiber industrial oil agents.
By adopting the technical scheme, the cardanol polyoxyethylene ether prepared by the method is applied to washing of the cleaning agent, so that the cleaning performance of the cleaning agent can be improved, and foams generated by the cleaning agent are less; the detergent is applied to the printing and dyeing industry, and is suitable for a new washing and dyeing integrated process due to excellent high-temperature washing resistance; because of good wettability, the water-soluble polyurethane emulsion can be applied to textile refining agents, coating additives, wetting agents in pesticide chemicals and emulsifying agents in pesticide chemicals; the antistatic agent is applied to synthetic fiber industrial oiling agents, and has good emulsifying performance and an antistatic effect.
In summary, the present application has the following beneficial effects:
1. according to the preparation method, the organic base catalyst and the inorganic base catalyst are respectively used for preparing the cardanol polyoxyethylene ether through segmented addition, so that the number of epoxy ethane molecules in the cardanol polyoxyethylene ether is increased, the prepared cardanol polyoxyethylene ether has the advantage of wide molecular weight distribution, and the application range of the cardanol polyoxyethylene ether is expanded;
2. the triethylamine catalyst is preferably adopted in the application, has stable performance, can accelerate the polymerization reaction rate, does not participate in the polymerization reaction, has stable and controllable catalytic reaction, generates an intermediate product with small and stable molecular weight and small double bond loss, and is an ideal organic base catalyst;
3. according to the method, the number of the ethylene oxide molecules to be added can be designed according to application requirements so as to adjust the hydrophilic balance of the product, and the prepared cardanol polyoxyethylene ether can be well applied to the fields of textile printing and dyeing, daily washing, metal washing and the like.
Detailed Description
The present application will be described in further detail with reference to examples.
The cardanol in the embodiment of the application is collected from the chemical Limited Nanjing Chihua, and the purity specification is 99.95%;
ethylene oxide was obtained from Shanghai Aladdin Biotechnology GmbH with a purity of 99.5%;
triethylamine was collected from Shanghai Aladdin Biotechnology Ltd with a purity of 99.5%;
the potassium hydroxide is collected from the fine chemical company Limited of the corridor Peng color and is analytically pure.
Examples
Example 1: the cardanol polyoxyethylene ether is prepared by the following steps:
s1, adding 302g of cardanol into a reactor, replacing air in the reactor for 3 times by a nitrogen-filled and vacuumizing device, heating to 90 ℃ while stirring, then carrying out vacuum dehydration for 30min, filling nitrogen into the reactor to normal pressure after dehydration, adding 0.604g of triethylamine catalyst, continuously introducing 88g of ethylene oxide for reaction at the temperature of 130 ℃ and under the pressure condition of 0.1MPa within 2h, curing for 1h after the reaction is finished, cooling to 90 ℃, and degassing to obtain an intermediate product;
s2, supplementing nitrogen to normal pressure, adding 0.604g of potassium hydroxide, continuously introducing 308g of ethylene oxide for reaction at the temperature of 130 ℃ and under the pressure condition of 0.1MPa within 2h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing, continuously cooling to 70 ℃, and neutralizing with 17.5mol/L glacial acetic acid until the pH value is approximately equal to 6 to obtain the cardanol polyoxyethylene ether.
Example 2: the cardanol polyoxyethylene ether is prepared by the following steps:
s1, adding 302g of cardanol into a reactor, replacing air in the reactor with a nitrogen-filled and vacuumizing device for 4 times, heating to 95 ℃ while stirring, then carrying out vacuum dehydration for 30min, filling nitrogen into the reactor to normal pressure after dehydration, adding 0.906g of triethylamine catalyst, continuously introducing 110g of ethylene oxide for reaction at the temperature of 135 ℃ and under the pressure condition of 0.2MPa within 3h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing to obtain an intermediate product, and supplementing nitrogen to normal pressure;
and S2, supplementing nitrogen to normal pressure, adding 0.906g of potassium hydroxide, continuously introducing 2200g of ethylene oxide for reaction at the temperature of 135 ℃ under the pressure condition of 0.2MPa within 3h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing, continuously cooling to 70 ℃, and neutralizing with 17.5mol/L glacial acetic acid until the pH value is approximately equal to 6 to obtain the cardanol polyoxyethylene ether.
Example 3: the cardanol polyoxyethylene ether is prepared by the following steps:
s1, adding 302g of cardanol into a reactor, replacing air in the reactor with a nitrogen-filled and vacuumizing device for 4 times, heating to 100 ℃ while stirring, then carrying out vacuum dehydration for 30min, filling nitrogen into the reactor to normal pressure after dehydration, adding 1.208g of triethylamine catalyst, continuously introducing 132g of ethylene oxide for reaction at the temperature of 140 ℃ and under the pressure condition of 0.3MPa within 4h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing to obtain an intermediate product, and supplementing nitrogen to normal pressure;
s2, supplementing nitrogen to normal pressure, adding 1.208g of potassium hydroxide, continuously introducing 4400g of ethylene oxide for reaction at the temperature of 140 ℃ and under the pressure condition of 0.3MPa within 4h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing, continuously cooling to 70 ℃, and neutralizing with 17.5mol/L glacial acetic acid until the pH value is approximately equal to 6 to obtain the cardanol polyoxyethylene ether.
Comparative example
Comparative example 1: the cardanol polyoxyethylene ether is prepared by the following steps:
s1, adding 302g of cardanol into a reactor, replacing air in the reactor with a nitrogen-filled and vacuumizing device for 4 times, heating to 95 ℃ while stirring, then carrying out vacuum dehydration for 30min, filling nitrogen into the reactor to normal pressure after dehydration, adding 0.906g of triethylamine catalyst, continuously introducing 2310g of ethylene oxide for reaction at the temperature of 135 ℃ and under the pressure condition of 0.2MPa within 3h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing, continuously cooling to 70 ℃, and neutralizing with 17.5mol/L glacial acetic acid until the pH value is approximately equal to 6 to obtain cardanol polyoxyethylene ether.
Comparative example 2: the cardanol polyoxyethylene ether is prepared by the following steps:
s1, adding 302g of cardanol into a reactor, replacing air in the reactor with a nitrogen-filled and vacuumizing device for 4 times, heating to 95 ℃ while stirring, then carrying out vacuum dehydration for 30min, filling nitrogen into the reactor to normal pressure after dehydration, adding 0.906g of potassium hydroxide catalyst, continuously introducing 2310g of ethylene oxide for reaction at the temperature of 135 ℃ and under the pressure of 0.2MPa within 3h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing, continuously cooling to 70 ℃, and neutralizing with 17.5mol/L glacial acetic acid until the pH value is approximately equal to 6 to obtain cardanol polyoxyethylene ether.
Comparative example 3: the cardanol polyoxyethylene ether is prepared by the following steps:
s1, adding 302g of cardanol into a reactor, replacing air in the reactor with a nitrogen-filled and vacuumizing device for 4 times, heating to 95 ℃ while stirring, then carrying out vacuum dehydration for 30min, filling nitrogen into the reactor to normal pressure after dehydration, adding 0.906g of potassium hydroxide, continuously introducing 110g of ethylene oxide into the reactor for reaction at 135 ℃ and under the pressure condition of 0.2MPa within 3h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing to obtain an intermediate product, and supplementing nitrogen to normal pressure;
and S2, adding 0.906g of triethylamine, continuously introducing 2200g of ethylene oxide for reaction at the temperature of 135 ℃ under the pressure condition of 0.2MPa within 3h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing, continuously cooling to 70 ℃, and neutralizing with 17.5mol/L glacial acetic acid until the pH value is approximately equal to 6 to obtain the cardanol polyoxyethylene ether.
Comparative example 4: the cardanol polyoxyethylene ether is prepared by the following steps:
s1, adding 304g of cardanol into a reactor, replacing air in the reactor with a nitrogen-filled and vacuumizing device for 4 times, heating to 95 ℃ while stirring, then carrying out vacuum dehydration for 30min, filling nitrogen into the reactor to normal pressure after dehydration, adding 0.906g of sodium methoxide catalyst, continuously introducing 2310g of ethylene oxide for reaction at the temperature of 135 ℃ and under the pressure of 0.2MPa within 3h, curing for 1h after the reaction is finished, cooling to 90 ℃, degassing, continuously cooling to 70 ℃, and neutralizing with 17.5mol/L glacial acetic acid until the pH value is approximately equal to 6 to obtain cardanol polyoxyethylene ether.
Performance test
The cardanol polyoxyethylene ethers prepared in examples 1 to 3 and comparative examples 1 to 4 were respectively used as test samples, the molecular weight distribution data of the test samples were measured by gel permeation chromatography, and the molecular weight step index was calculated and is shown in the following table 1.
Fractional molecular weight index: a parameter D, called distribution index, representing the width of the molecular weight distribution; d ═ m (w)/m (n), where m (w) is the weight average molecular weight and m (n) is the number average molecular weight; when D is 1, it is a polymer having a uniform molecular weight, and the larger the value of D is than 1, the broader the molecular weight distribution is, and the larger the degree of polydispersity is.
The double bond retention of the test samples was determined using the iodine number method and is included in the following Table 1.
TABLE 1 molecular weight distribution index and double bond Retention Rate results
As can be seen from the test data in table 1: compared with comparative examples 1-4, the cardanol polyoxyethylene ether prepared in examples 1-3 has a higher molecular weight step index, which shows that the cardanol polyoxyethylene ether prepared in examples 1-3 has a wider molecular weight distribution and a wide application range, and meanwhile, the cardanol polyoxyethylene ether prepared in examples 1-3 has a higher double bond retention rate, which shows that the cardanol polyoxyethylene ether has good product quality and stable performance. Among them, example 2 is the most preferable example, and has a molecular weight distribution index as high as 1.48 and a double bond retention rate as high as 96.39%.
In the comparative example 1, cardanol and ethylene oxide are used as raw materials, triethylamine is used as a catalyst, the cardanol polyoxyethylene ether is prepared through one-step reaction, and the molecular weight step index of the product is only 1.19; in comparative example 2, cardanol and ethylene oxide were used as raw materials, potassium hydroxide was used as a catalyst, and the molecular weight fractional index of the product was only 1.21; in comparative example 4, cardanol and ethylene oxide were used as raw materials, sodium methoxide was used as a catalyst, and the molecular weight fractional index of the product was only 1.10. The molecular weight distribution indexes of the cardanol polyoxyethylene ether prepared in the embodiments 1-3 are all larger than 1.45, so that the cardanol polyoxyethylene ether prepared by the method has the advantages of wide molecular weight, high double bond retention rate, stable property and wide application range, and can be well applied to the fields of textile printing and dyeing, daily washing, metal washing and the like.
Combining example 2 and comparative example 3, and table 1, it can be seen that in comparative example 3, the molecular weight step index was 1.31 in the first stage reaction using potassium hydroxide as the catalyst, and in the second stage reaction using triethylamine as the catalyst, whereas in example 2, the molecular weight distribution index was as high as 1.48 in the first stage reaction using triethylamine as the catalyst, and in the second stage reaction using potassium hydroxide as the catalyst. Therefore, the use sequence of the catalysts can influence the molecular weight distribution of the obtained cardanol polyoxyethylene ether, and when the triethylamine catalyst is used firstly and then the potassium hydroxide catalyst is used, the prepared cardanol polyoxyethylene ether has a wider molecular weight, a wide application range, a high double bond retention rate and a more stable property.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.
Claims (10)
1. The cardanol polyoxyethylene ether is characterized by having a structural formula as follows:
wherein, R is a hydrocarbon chain containing 15 carbon atoms, and can be respectively a saturated hydrocarbon chain or an unsaturated hydrocarbon chain containing monoene, diene and triene shown as the following:
C15H31，
C15H29，
C15H27，
C15H25，
n＝3-30；
the cardanol polyoxyethylene ether is prepared by taking cardanol and ethylene oxide as raw materials and performing sectional addition on the cardanol polyoxyethylene ether by using an organic base catalyst and an inorganic base catalyst.
2. The preparation method of cardanol polyoxyethylene ether according to claim 1, characterized by comprising the following steps:
s1, heating and pressurizing cardanol and ethylene oxide under the action of an organic base catalyst to perform polymerization reaction, curing after the reaction is finished, and vacuumizing to remove the organic base catalyst to obtain an intermediate product;
and S2, continuously reacting the intermediate product with ethylene oxide, heating and pressurizing under the action of an inorganic base catalyst to perform polymerization reaction, curing after the reaction is finished, and adding acetic acid to neutralize to obtain the cardanol polyoxyethylene ether.
3. The preparation method of cardanol polyoxyethylene ether according to claim 2, wherein the specific steps of S1 are as follows: adding cardanol into a reactor, introducing nitrogen, ensuring that the reaction is carried out in a nitrogen environment, stirring and heating to 90-100 ℃, dehydrating, adding an organic base catalyst, introducing ethylene oxide, setting the reaction temperature at 130-140 ℃, setting the reaction pressure at 0.1-0.3MPa, reacting for 2-4h, post-curing, and vacuumizing to remove the organic base catalyst to obtain an intermediate product.
4. The preparation method of cardanol polyoxyethylene ether according to claim 3, wherein said organic base catalyst is triethylamine, and the amount of added triethylamine is 0.2-0.4% of the amount of added cardanol.
5. The method for preparing cardanol polyoxyethylene ether according to claim 4, wherein in S1, the molar ratio of cardanol to ethylene oxide is 1: (2-3).
6. The preparation method of cardanol polyoxyethylene ether according to claim 5, characterized in that the structural formula of the intermediate product is:
wherein, R is a hydrocarbon chain containing 15 carbon atoms, and can be respectively a saturated hydrocarbon chain or an unsaturated hydrocarbon chain containing monoene, diene and triene shown as the following:
C15H31，
C15H29，
C15H27，
C15H25，
n＝2-6。
7. the preparation method of cardanol polyoxyethylene ether according to claim 2, wherein the specific steps of S2 are as follows: adding an inorganic base catalyst into the reactor, introducing ethylene oxide, setting the reaction temperature at 130-140 ℃, setting the reaction pressure at 0.1-0.3MPa, reacting for 2-4h, curing, cooling, and adding acetic acid for neutralization to obtain the cardanol polyoxyethylene ether.
8. The preparation method of cardanol polyoxyethylene ether according to claim 7, wherein said inorganic base catalyst is potassium hydroxide, and the amount of added potassium hydroxide is 0.2-0.4% of the amount of added cardanol.
9. The preparation method of cardanol polyoxyethylene ether according to claim 8, wherein the molar ratio of ethylene oxide added in S2 to cashew in S1 is (7-100): 1.
10. The application of the cardanol polyoxyethylene ether as claimed in claim 1, wherein said cardanol polyoxyethylene ether is applied in industrial and civil cleaning agents, printing and dyeing industry, textile refining agents, coating additives, wetting agents in pesticide chemicals, emulsifying agents in pesticide chemicals, and oil agents in synthetic fiber industry.
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| CN113818106A (en) * | 2021-08-25 | 2021-12-21 | 浙江恒澜科技有限公司 | Environment-friendly degradable polyester FDY oil agent and preparation method thereof |
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