CN112142640A - Bola type surfactant with anion-cation reversal capability and preparation method thereof - Google Patents
Bola type surfactant with anion-cation reversal capability and preparation method thereof Download PDFInfo
- Publication number
- CN112142640A CN112142640A CN202011004763.5A CN202011004763A CN112142640A CN 112142640 A CN112142640 A CN 112142640A CN 202011004763 A CN202011004763 A CN 202011004763A CN 112142640 A CN112142640 A CN 112142640A
- Authority
- CN
- China
- Prior art keywords
- reaction
- surfactant
- anion
- bola
- external environment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Abstract
The invention discloses a Bola type surfactant with anion-cation reversal capability and a preparation method thereof, wherein the preparation method comprises the following steps: 1) adding 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride into a three-neck flask, introducing nitrogen, and performing nucleophilic addition-elimination reaction to generate imide; followed by LiAlH4Reducing carbonyl group. 2) Diluting the product, adding potassium permanganate, heating to perform oxidation reaction to generate carboxyl; after the reaction is finished, sodium sulfite is added to remove excessive potassium permanganate, diatomite is adopted for filtration, ethyl acetate is adopted for extracting impurities, a water phase is collected, and the water phase is filtered and dried to constant weight to obtain a final product. The surfactant has excellent anion-cation reversal characteristics, and the type of the surfactant can be changed according to the external environment. The anionic surfactant is used under the condition that the external environment is alkaline, and the cationic surfactant is used under the condition that the external environment is acidic.
Description
Technical Field
The invention belongs to the field of functional surfactants, and particularly relates to a Bola type surfactant with anion-cation reversal capacity and a preparation method thereof.
Background
The surfactant is an amphiphilic compound containing a nonpolar oleophilic group and a polar hydrophilic group in a molecular structure, can form directional arrangement on a gas-liquid interface and a solid-liquid interface, can remarkably reduce the surface tension of the solution by adding a small amount of the surfactant into the solution, and effectively changes the physical and chemical properties of the interface. Therefore, the method is widely applied to the fields of daily life, industry and agriculture, high and new technology and the like, and becomes one of important industries of chemical processes. The surfactant industry still has the defects of single variety, simple structure, laggard process and the like due to the long-standing weak foundation.
Disclosure of Invention
In order to enrich the types of surfactants and endow the surfactants with functionalization, the invention designs and prepares a Bola type surfactant with anion-cation reversal capability and a preparation method thereof.
In order to achieve the purpose, the invention adopts the following technical means:
a Bola type surfactant with anion-cation reversal capability has a structural formula as follows:
the surfactant reverses the properties of anions and cations according to the change of the pH value of the external environment.
The Bola type surfactant is an anionic surfactant under the condition that the external environment is alkaline, and is a cationic surfactant under the condition that the external environment is acidic.
A preparation method of a Bola type surfactant with anion-cation reversal capability comprises the following steps:
mixing 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride, introducing nitrogen, and performing nucleophilic addition-elimination reaction at 150-200 ℃ to generate imide; followed by LiAlH4Reducing carbonyl by a reducing agent at 0-35 ℃;
adding potassium permanganate into the product after carbonyl reduction, and heating to 90-100 ℃ to perform oxidation reaction to generate carboxyl; and after the reaction is finished, carrying out post-treatment to obtain a final product.
As a further improvement of the present invention, the molar ratio of 1, 12-diaminododecane to cyclobutane-3-enedicarboxylic anhydride in the nucleophilic addition-elimination reaction is 1: 4.
As a further improvement of the invention, in the reduction reaction, LiAlH4The molar ratio of the 1, 12-diaminododecane to the N-methyl-dodecyl-benzene-N-methyl-ethyl-benzene-N-methyl-dodecane is 2-2.4: 1.
As a further improvement of the invention, in the oxidation reaction, the amount of the substance of the potassium permanganate is 2-4 times of the amount of the substance of the 1, 12-diaminododecane.
As a further improvement of the invention, in the oxidation reaction, after the product after carbonyl reduction is diluted, potassium permanganate is slowly added at 0 ℃, and then the temperature is raised for reaction.
As a further improvement of the invention, the post-treatment comprises:
and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate, filtering by adopting diatomite and extracting impurities by adopting ethyl acetate, collecting a water phase, adjusting the pH value to be 2-4 to separate out a product, and filtering and drying to constant weight to obtain a final product.
Compared with the prior surfactant, the invention has the following advantages:
the Bola type surfactant with the anion-cation reversal capability prepared by the invention can be applied to the fields of oil exploitation, crude oil recovery, soil remediation and the like. The surfactant has excellent anion-cation reversal characteristics, and the type of the surfactant can be changed according to the external environment. The anionic surfactant is used under the condition that the external environment is alkaline, and the cationic surfactant is used under the condition that the external environment is acidic.
The surfactant can realize the reversal of the properties of anions and cations according to the change of the pH value of the external environment, and particularly, the Bola type surfactant with the anion and cation reversal capability is an anionic surfactant under the alkaline condition of the external environment and is a cationic surfactant under the acidic condition of the external environment.
Drawings
FIG. 1 is a synthetic scheme of the Bola type surfactant having a cation-anion reversal ability obtained in example 4.
FIG. 2 is a graph showing the change of surface tension with pH of the Bola type surfactant having a cation-anion reversal ability obtained in example 4.
Detailed Description
The invention relates to a Bola type surfactant with anion-cation reversal capability, the reaction equation of the preparation process is as follows:
according to the reaction mechanism, the invention adopts the following technical scheme:
a Bola type surfactant with anion-cation reversal capability, the structural formula of the surfactant is as follows:
the method for preparing the Bola type surfactant with the anion-cation reversal capability comprises the following steps:
1) dropwise adding 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride in sequence into a three-neck flask provided with a reflux condenser pipe, introducing nitrogen, reacting for 2-5 h at 150-200 ℃, and performing a first-step nucleophilic addition-elimination reaction to generate imide, wherein the molar ratio of the 1, 12-diaminododecane to the cyclobut-3-ene dicarboxylic anhydride is 1: 4; followed by LiAlH4Reduction of imide for reducing agent, in which LiAlH4The molar ratio of the 1, 12-diaminododecane to the N-hydroxydodecane is 2-2.4: 1, the reduction temperature is 0-35 ℃, and the reduction time is 4-6 hours.
2) Diluting the product, slowly adding potassium permanganate at 0 ℃, heating and reacting for 10-12 h, wherein the amount of potassium permanganate is 2-4 times that of 1, 12-diaminododecane; and reducing excessive potassium permanganate by using sodium sulfite, dropwise adding dilute hydrochloric acid until the pH of the reaction solution is 2-4, separating out the product, and filtering and drying to constant weight to obtain the final product.
The surfactant can realize reversal of anion and cation properties according to the change of external environment pH.
The inversion principle of the Bola type surfactant with the anion-cation inversion capability is realized by the following reactions:
the Bola type surfactant with the anion-cation reversal capability is an anionic surfactant under the condition that the external environment is alkaline, and is a cationic surfactant under the condition that the external environment is acidic.
The technical solution in the embodiments of the present invention will be clearly and completely described below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (49.6g, 0.4mol) were added dropwise in this order to a 250mL three-necked flask equipped with a reflux condenser, and nitrogen was introduced 3 times, followed by heating to 180 ℃ for 3 hours and monitoring the completion of the reaction by TLC (Thin Layer Chromatography). After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) 80mL of tetrahydrofuran dried with sodium metal were charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 7.6g of LiAlH were slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and raising the temperature to 25 ℃ after the addition is finished to react for 4 h. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 7.6mLH under ice salt bath2O, 7.6mL 15% aqueous NaOH and 22.8mLH2O quenching excess LiAlH4Filtering, washing the filter cake with ethyl acetate, filteringDrying the solution with anhydrous magnesium sulfate, concentrating under reduced pressure to obtain crude product, and separating with column to obtain the final product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in an ice salt bath, cooling to 0 ℃, and slowly adding potassium permanganate KMnO4(40g, the adding time is 40min), after all the components are added, slowly raising the temperature to 90 ℃ for reaction for 12 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 2 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure final product.
The product obtained in example 1 is obtained in 59% yield.
Example 2
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (49.6g, 0.4mol) were added dropwise in this order to a 250mL three-necked flask equipped with a reflux condenser, and nitrogen was introduced 3 times, followed by heating to 150 ℃ for 2 hours and monitoring the completion of the reaction by TLC (Thin Layer Chromatography). After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) 90mL of tetrahydrofuran dried with sodium metal were charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 8.36g of LiAlH were slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and raising the temperature to 30 ℃ after the addition for reaction for 5 h. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 8.4mLH into the mixture under ice salt bath2O, 8.4mL 15% aqueous NaOH and 25.2mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by using ethyl acetate, drying the filtrate by using anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain a product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in an ice salt bath, cooling to 0 ℃, and slowly adding potassium permanganate KMnO4(31.6g, the addition time is 40min), and after the addition is finished, the temperature is slowly raised to 100 ℃ for reaction for 10 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 3 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure final product.
The product obtained in example 2 was obtained in 53% yield.
Example 3
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (49.6g, 0.4mol) were added dropwise in this order to a 250mL three-necked flask equipped with a reflux condenser, and nitrogen was introduced 3 times, followed by heating to 200 ℃ for 5 hours and monitoring the completion of the reaction by TLC (Thin Layer Chromatography). After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imine.
(2) 100mL of tetrahydrofuran dried with sodium metal was charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 9.12g of LiAlH was slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and raising the temperature to 35 ℃ after the addition for reacting for 6 h. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 9.2mLH under ice salt bath2O, 9.2mL 15% aqueous NaOH and 27.6mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by using ethyl acetate, drying the filtrate by using anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain a product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in a salt-ice bath, cooling to 0 ℃, and slowingSlowly adding potassium permanganate KMnO4(50g, the adding time is 40min), and after the adding is finished, slowly raising the temperature to 90 ℃ for reaction for 12 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 4 by using dilute hydrochloric acid to precipitate solids, and filtering and drying to obtain a pure final product.
The product obtained in example 3 is obtained in 54% yield.
Example 4
(1) 1, 12-diaminododecane (20.0g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (49.6g, 0.4mol) were added dropwise in this order to a 250mL three-necked flask equipped with a reflux condenser, and nitrogen was introduced 3 times, followed by heating to 190 ℃ for 5 hours and monitoring the completion of the reaction by TLC (Thin Layer Chromatography). After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) 80mL of tetrahydrofuran dried with sodium metal were charged into a 250mL three-necked flask, cooled to 0 ℃ using a cold salt bath, and 9.5g of LiAlH were slowly added in portions4After stirring for 3min, slowly dropwise adding the imide dissolved in tetrahydrofuran into a three-neck flask, and raising the temperature to 25 ℃ after the addition is finished to react for 6 h. The completion of the reaction was monitored by TLC (thinLayerChromatography). After the reaction is finished, cooling to 0 ℃, and sequentially adding 9.5mLH into the mixture under ice salt bath2O, 9.5mL 15% aqueous NaOH and 28.5mLH2O quenching excess LiAlH4Filtering, fully washing a filter cake by using ethyl acetate, drying the filtrate by using anhydrous magnesium sulfate, concentrating under reduced pressure to obtain a crude product, and finally separating by using a column to obtain a product.
(3) Adding the product and 80mL of distilled water into a 250mL three-neck flask, placing the three-neck flask in an ice salt bath, cooling to 0 ℃, and slowly adding potassium permanganate KMnO4(63.2g, adding time is 40min), after all the materials are added, slowly raising the temperature to 100 ℃ for reactionAnd (5) 10 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 2 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure final product.
The product obtained in example 4 was obtained in 62% yield.
In order to characterize the structural characteristics of a Bola-type surfactant with the anion-cation reversal ability, the Bola-type surfactant with the anion-cation reversal ability synthesized in example 4 was subjected to nuclear magnetic hydrogen spectrum test, and the results are shown below:
1H NMR(300MHz,DMSO):12.13(s,4H),2.78-2.43(m,16H),1.36-1.26(m,20H)ppm。
to characterize the surface tension of a Bola-type surfactant with the ability to reverse the cation and anion. The JK99C full-automatic surface tensiometer measures the surface tension of the surfactant solution. First, a surfactant solution having a concentration of 0.01mol/L was prepared, and the surface tension thereof was measured at 25 ℃. Continuously reading 5 data with rise and fall in the testing process, wherein the difference of the 5 data is less than 1, taking the average value of the data as the final surface tension value of the solution, and the testing method is a platinum ring method.
As shown in fig. 2, the surface tension of the surfactant solution is a function of pH. As can be seen, as the pH of the surfactant solution increases, its surface tension increases and then decreases. When the pH is 6, the surface tension reaches a maximum of 64.1mN/m, indicating that the surfactant has a strong surface activity under acidic or alkaline conditions.
The foregoing is a more detailed description of the invention and it is not intended that the invention be limited to the specific embodiments described herein, but that various modifications, alterations, and substitutions may be made by those skilled in the art without departing from the spirit of the invention, which should be construed to fall within the scope of the invention as defined by the appended claims.
Claims (9)
1. A Bola type surfactant with anion-cation reversal capability is characterized in that the structural formula is as follows:
2. the Bola-type surfactant according to claim 1, wherein the anionic and cationic properties of the surfactant are reversed according to a change in pH of an external environment.
3. The Bola-type surfactant according to claim 2, wherein the Bola-type surfactant is an anionic surfactant under an alkaline external environment, and is a cationic surfactant under an acidic external environment.
4. A preparation method of a Bola type surfactant with anion-cation reversal capability is characterized by comprising the following steps:
mixing 1, 12-diaminododecane and cyclobut-3-ene dicarboxylic anhydride, introducing nitrogen, and performing nucleophilic addition-elimination reaction at 150-200 ℃ to generate imide; followed by LiAlH4Reducing carbonyl by a reducing agent at 0-35 ℃;
adding potassium permanganate into the product after carbonyl reduction, and heating to 90-100 ℃ to perform oxidation reaction to generate carboxyl; and after the reaction is finished, carrying out post-treatment to obtain a final product.
5. The method according to claim 4, wherein the molar ratio of 1, 12-diaminododecane to cyclobutane-3-enedicarboxylic anhydride is 1:4 in the nucleophilic addition-elimination reaction.
6. The method according to claim 4, wherein LiAlH is added to the reaction mixture in the reduction reaction4With 1, 12-diaminododecaneThe molar ratio is 2-2.4: 1.
7. The method according to claim 4, wherein the amount of potassium permanganate is 2 to 4 times the amount of 1, 12-diaminododecane in the oxidation reaction.
8. The preparation method according to claim 4, wherein in the oxidation reaction, after the product after carbonyl reduction is diluted, potassium permanganate is slowly added at 0 ℃, and then the temperature is raised for reaction.
9. The method of manufacturing according to claim 4, wherein the post-treatment comprises:
and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate, filtering by adopting diatomite and extracting impurities by adopting ethyl acetate, collecting a water phase, adjusting the pH value to be 2-4 to separate out a product, and filtering and drying to constant weight to obtain a final product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011004763.5A CN112142640B (en) | 2020-09-22 | 2020-09-22 | Bola type surfactant with anion-cation reversal capability and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011004763.5A CN112142640B (en) | 2020-09-22 | 2020-09-22 | Bola type surfactant with anion-cation reversal capability and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112142640A true CN112142640A (en) | 2020-12-29 |
| CN112142640B CN112142640B (en) | 2022-07-22 |
Family
ID=73897743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011004763.5A Active CN112142640B (en) | 2020-09-22 | 2020-09-22 | Bola type surfactant with anion-cation reversal capability and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112142640B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112125833A (en) * | 2020-09-22 | 2020-12-25 | 陕西科技大学 | Bola type surfactant with self-demulsification capacity and preparation method and application thereof |
| CN112138604A (en) * | 2020-09-22 | 2020-12-29 | 陕西科技大学 | Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof |
| CN114229979A (en) * | 2022-02-18 | 2022-03-25 | 河南博源新材料有限公司 | Polyacrylamide composition containing Bola type cationic surfactant, preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2961093A1 (en) * | 2010-06-09 | 2011-12-16 | Oreal | COSMETIC COMPOSITION COMPRISING A POLYMER AND A 4-CARBOXY 2-PYRROLIDINONE DERIVATIVE, COSMETIC TREATMENT METHOD AND COMPOUND |
| FR2961100A1 (en) * | 2010-06-09 | 2011-12-16 | Oreal | Use of 2-pyrrolidone compounds as a cosmetic active solubilization agent including assets of care for the keratin fibers |
| CN103242216A (en) * | 2013-05-07 | 2013-08-14 | 兰州梦唐精细化工有限公司 | Synthesis method of N-Boc-hexahydro-5-oxo-cyclopenta (C) pyrrole |
| CN103998424A (en) * | 2011-12-15 | 2014-08-20 | 陶氏环球技术有限责任公司 | Process for preparing alkyl pyroglutamic acids |
| JP6372118B2 (en) * | 2014-03-18 | 2018-08-15 | 東洋インキＳｃホールディングス株式会社 | Amphoteric surfactant and process for producing the same |
-
2020
- 2020-09-22 CN CN202011004763.5A patent/CN112142640B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2961093A1 (en) * | 2010-06-09 | 2011-12-16 | Oreal | COSMETIC COMPOSITION COMPRISING A POLYMER AND A 4-CARBOXY 2-PYRROLIDINONE DERIVATIVE, COSMETIC TREATMENT METHOD AND COMPOUND |
| FR2961100A1 (en) * | 2010-06-09 | 2011-12-16 | Oreal | Use of 2-pyrrolidone compounds as a cosmetic active solubilization agent including assets of care for the keratin fibers |
| CN103998424A (en) * | 2011-12-15 | 2014-08-20 | 陶氏环球技术有限责任公司 | Process for preparing alkyl pyroglutamic acids |
| CN103242216A (en) * | 2013-05-07 | 2013-08-14 | 兰州梦唐精细化工有限公司 | Synthesis method of N-Boc-hexahydro-5-oxo-cyclopenta (C) pyrrole |
| JP6372118B2 (en) * | 2014-03-18 | 2018-08-15 | 東洋インキＳｃホールディングス株式会社 | Amphoteric surfactant and process for producing the same |
Non-Patent Citations (3)
| Title |
|---|
| M. S. RAASCH ET AL.: "2，2-DIFLUOROSUCCINIC ACID", 《ORGANIC SYNTHESES》 * |
| YUBIN ZHAO ET AL.: "Study on tunable crosslinking anion exchange membranes fabrication and degradation mechanism", 《INTERNATIONAL JOURNAL OF HYDROGEN ENERGY》 * |
| 钱建华: "《精细化学品化学》", 31 December 2010, 东北大学出版社 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112125833A (en) * | 2020-09-22 | 2020-12-25 | 陕西科技大学 | Bola type surfactant with self-demulsification capacity and preparation method and application thereof |
| CN112138604A (en) * | 2020-09-22 | 2020-12-29 | 陕西科技大学 | Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof |
| CN114229979A (en) * | 2022-02-18 | 2022-03-25 | 河南博源新材料有限公司 | Polyacrylamide composition containing Bola type cationic surfactant, preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112142640B (en) | 2022-07-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112142640B (en) | Bola type surfactant with anion-cation reversal capability and preparation method thereof | |
| JPS5850775B2 (en) | Production method of copper-iron-aluminum catalyst | |
| CN103055883A (en) | Supported nickel-based catalyst and its preparation method and use | |
| JP2012502891A (en) | Preparation of azo compounds using solid catalysts | |
| CN112138604B (en) | Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof | |
| CN111992133B (en) | Tricarboxy amphoteric surfactant and preparation method thereof | |
| CN107141490B (en) | Two-dimensional structure 4- (1H-tetrazole-5-yl) zinc benzoate coordination polymer and synthesis method and application thereof | |
| CN111992134B (en) | Polycarboxyl amphoteric Bola type surfactant and preparation method thereof | |
| CN112125831B (en) | Tetra-amide nonionic surfactant and synthesis method thereof | |
| CN107790191B (en) | Preparation method of solid acid catalyst for cyclohexanone and ethylene ketal reaction | |
| CN112125833B (en) | Bola type surfactant with self-demulsification capacity and preparation method and application thereof | |
| CN111122482A (en) | Preparation method of substituted polyacetylene type water-phase divalent copper ion detection probe, product and application thereof | |
| Patle et al. | An eco-friendly synthesis, characterization, morphology and ion exchange properties of terpolymer resin derived from p-hydroxybenzaldehyde | |
| CN112079761B (en) | Bisamide nonionic surfactant and synthesis method and application thereof | |
| CN112079762B (en) | Surfactant with self-demulsification capability and preparation method and application thereof | |
| Rahangdale et al. | Chelation ion exchange properties of 2, 4-dihydroxyacetophenone-biuret-formaldehyde terpolymer resin | |
| Rahangdale et al. | Synthesis and chelation ion exchange properties of 2, 4-dihydroxyacetophenone-biuret-formaldehyde terpolymer resin | |
| Masram et al. | Synthesis of resin I: salicylic acid, hexamethylene diamine and formaldehyde and its ion-exchange properties | |
| CN112125830A (en) | Polyamide compound and preparation method thereof | |
| CN111454551A (en) | Application of imidazolyl molybdate ionic liquid in preparation of P LL A/I L s blend | |
| CN111995559A (en) | Hexacarboxy chelating agent and preparation method thereof | |
| CN108329317B (en) | Phenanthroline derivative and preparation method and application thereof | |
| Gupta et al. | Synthesis, Characterization and Ion-Exchange Properties of Terpolymer Resin-II Derived from p-Hydroxybenzaldehyde, Thiourea and Ethylene Glycol | |
| CN114438528B (en) | Electrochemical preparation method of benzanthrone | |
| CN114349753B (en) | Fluorescent probe for detecting zinc ions and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20230411 Address after: No.55 Qingyang Road, Qingcheng County, Qingyang City, Gansu Province, 745199 Patentee after: Qingyang Bainachuan New Material Technology Co.,Ltd. Address before: 710021 Shaanxi province Xi'an Weiyang University Park Patentee before: SHAANXI University OF SCIENCE & TECHNOLOGY |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20230830 Address after: 745112 Fucheng street, sanliupu Town, Qingcheng County, Qingyang City, Gansu Province Patentee after: Gansu Zhilun New Material Technology Co.,Ltd. Address before: No.55 Qingyang Road, Qingcheng County, Qingyang City, Gansu Province, 745199 Patentee before: Qingyang Bainachuan New Material Technology Co.,Ltd. |