CN111111552A - Malathion-based saccharide surfactant and preparation method and application thereof - Google Patents
Malathion-based saccharide surfactant and preparation method and application thereof Download PDFInfo
- Publication number
- CN111111552A CN111111552A CN201911302963.6A CN201911302963A CN111111552A CN 111111552 A CN111111552 A CN 111111552A CN 201911302963 A CN201911302963 A CN 201911302963A CN 111111552 A CN111111552 A CN 111111552A
- Authority
- CN
- China
- Prior art keywords
- rosin
- maleated rosin
- maleated
- surfactant
- preparation
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/027—Keto-aldonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/033—Uronic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Saccharide Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention discloses a maleated rosin based sugar surfactant, a preparation method and application thereof. The maleic rosin-based saccharide surfactant has the structural formula:
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to a maleated rosin-based saccharide surfactant as well as a preparation method and application thereof.
Background
Rosin is an important forestry resource, belongs to a reproducible natural product, and has the advantages of rich source, low price, biodegradability and the like. The rosin has a ternary phenanthrene ring structure and has better oleophylic property; the rosin is grafted with hydrophilic groups to obtain the surfactant with excellent performance. The maleic rosin is also called maleic anhydride rosin and is a product obtained by the addition reaction of rosin and maleic anhydride (maleic anhydride). The synthesis process of the maleated rosin is mature, and the mass production is realized at present. The maleated rosin is a high-performance modified rosin, and compared with rosin, the maleated rosin has the advantages that the carbon number is further increased, and the hydrophobicity can be improved. The study of synthesizing the rosin-based surfactant with high added value by using the maleic rosin as the raw material can realize high-value utilization of rosin resources, and the study is widely concerned.
Sugar is also an important bio-based resource, can be obtained from lignocellulose resources, and has the advantages of rich source, low price, biodegradability and the like. Sugars have a better hydrophilicity. The rosin-based saccharide surfactant can be obtained by combining maleic rosin with a sugar. The rosin-based saccharide surfactant belongs to a green bio-based surfactant and has wide application. However, the current research on rosin-based saccharide surfactants mainly focuses on rosin sucrose ester surfactants. Therefore, how to develop a novel rosin-based saccharide surfactant becomes a hot topic of interest for researchers in the field, and has important application significance.
Disclosure of Invention
In order to overcome the problems in the prior art, the invention aims at providing a maleic rosin-based sugar surfactant, the invention aims at providing a preparation method of the maleic rosin-based sugar surfactant, and the invention aims at providing the application of the maleic rosin-based sugar surfactant.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention provides a maleated rosin-based saccharide surfactant, which has a structural formula shown as a formula (1):
in the formula (1), n is 2-4; r is Glucarate (GLU) or Lactobionate (LAC).
Further, in the formula (1), n is selected from 2, 3 or 4.
Such maleated rosin-based saccharide surfactants of the present invention may be represented by MR-DN-n-R, where n is 2, 3 or 4; r ═ GLU or LAC.
The invention also provides a preparation method of the maleated rosin based saccharide surfactant.
A preparation method of maleated rosin-based sugar surfactant comprises the following steps:
1) reacting maleated rosin with an acyl chlorination reagent to obtain maleated rosin acyl chloride;
2) reacting maleated rosin acyl chloride with methanol to obtain maleated rosin methyl ester;
3) reacting maleic rosin methyl ester with diamine to obtain maleic rosin imide;
4) reacting maleated rosin imide with sugar acid or sugar acid lactone to obtain the maleated rosin-based saccharide surfactant.
Preferably, in step 1) of the preparation method of the maleated rosin-based sugar surfactant, the acyl chlorination reagent is selected from at least one of oxalyl chloride and thionyl chloride.
Preferably, in the preparation method step 1) of the maleated rosin-based saccharide surfactant, the molar ratio of the acyl chloride reagent to the maleated rosin is (1.5-5): 1; more preferably, the mole ratio of the acyl chlorination reagent to the maleated rosin is (2-4): 1.
preferably, in step 1) of the preparation method of the maleated rosin-based saccharide surfactant, a maleated rosin solution is reacted.
Preferably, in the preparation method of the maleated rosin-based saccharide surfactant, in the step 1), the maleated rosin concentration of the maleated rosin solution is 0.1 mol/L-1 mol/L; further preferably, the concentration of the maleated rosin in the maleated rosin solution is 0.4mol/L to 0.6 mol/L.
Preferably, in the preparation method of the maleated rosin-based saccharide surfactant, in the step 1), the solvent of the maleated rosin solution is benzene solvent; further preferably, the solvent of the maleated rosin solution is toluene.
Preferably, in the preparation method of the maleated rosin-based saccharide surfactant, in the step 1), the reaction temperature is 70-90 ℃, and the reaction time is 1.5-5 h; more preferably, the reaction temperature is 75-85 ℃, and the reaction time is 2-4 h.
Preferably, in the step 2) of the preparation method of the maleated rosin-based saccharide surfactant, a maleated rosin acyl chloride solution is reacted.
Preferably, in the step 2) of the preparation method of the maleated rosin-based saccharide surfactant, the concentration of the maleated rosin acyl chloride in the maleated rosin acyl chloride solution is 0.1 mol/L-1 mol/L; more preferably, the concentration of the maleic rosin acyl chloride in the maleic rosin acyl chloride solution is 0.4 mol/L-0.6 mol/L.
Preferably, in the step 2) of the preparation method of the maleated rosin-based saccharide surfactant, the solvent of the maleated rosin acyl chloride solution is a halogenated hydrocarbon solvent; further preferably, the solvent of the maleated rosin acyl chloride solution is dichloromethane.
In the step 2) of the preparation method of the maleated rosin-based saccharide surfactant, the amount of the methanol is suitable for the reaction and can be controlled according to actual needs.
Preferably, in the step 2) of the preparation method of the maleated rosin-based saccharide surfactant, an acid-binding agent is added to participate in the reaction; the molar ratio of the acid-binding agent to the maleated rosin acyl chloride is (1-3): 1, preferably (1.5-2.5): 1; the acid scavenger is preferably triethylamine.
Preferably, in the step 2) of the preparation method of the maleated rosin-based saccharide surfactant, the reaction temperature is 30-50 ℃, and the reaction time is 5-20 h; more preferably, in the step 2), the reaction temperature is 35-45 ℃ and the reaction time is 8-12 h.
Preferably, in step 3) of the preparation method of the maleated rosin-based saccharide surfactant, the diamine is at least one selected from ethylenediamine, propylenediamine and butylenediamine. The diamine can be represented by H2N(CH2)nNH2And n is 2, 3 or 4.
Preferably, in step 3) of the preparation method of the maleated rosin-based saccharide surfactant, a solution of methyl maleated rosin ester is reacted.
Preferably, in the step 3) of the preparation method of the maleated rosin-based saccharide surfactant, the concentration of the maleated rosin methyl ester in the maleated rosin methyl ester solution is 0.2 mol/L-2 mol/L; further preferably, the concentration of the maleic rosin methyl ester in the maleic rosin methyl ester solution is 0.8mol/L to 1.2 mol/L.
Preferably, in the step 3) of the preparation method of the maleated rosin-based saccharide surfactant, the solvent of the maleated rosin methyl ester solution is an alcohol solvent; further preferably, the solvent of the maleic rosin methyl ester solution is ethanol.
Preferably, in the step 3) of the preparation method of the maleated rosin-based saccharide surfactant, the molar ratio of the diamine to the maleated rosin methyl ester is (0.5-1.5): 1; more preferably, the molar ratio of the diamine to the methyl maleated rosin is (0.8-1.2): 1.
preferably, in the step 3) of the preparation method of the maleated rosin-based saccharide surfactant, the reaction temperature is 80-100 ℃, and the reaction time is 5-20 h; more preferably, in the step 3), the reaction temperature is 85-95 ℃ and the reaction time is 10-15 h.
Preferably, in step 4) of the preparation method of the maleated rosin-based saccharide surfactant, the reaction is carried out in an alcohol solvent.
Preferably, in step 4) of the preparation method of the maleated rosin-based saccharide surfactant, the alcohol solvent is selected from at least one of methanol and ethanol.
Preferably, in the step 4) of the preparation method of the maleated rosin-based saccharide surfactant, the concentration of the maleated rosin imide in the alcohol solvent is 0.01mol/L to 10 mol/L.
Preferably, in the step 4) of the preparation method of the maleated rosin-based saccharide surfactant, the molar ratio of the sugar acid or the sugar acid lactone to the maleated rosin imide is (0.8-1.2): 1.
preferably, in step 4) of the preparation method of the maleated rosin-based saccharide surfactant, the sugar acid is at least one selected from gluconic acid and lactobionic acid; the gluconolactone is gluconolactone.
Preferably, in the step 4) of the preparation method of the maleated rosin-based saccharide surfactant, the reaction temperature is 60-90 ℃, and the reaction time is 10-72 h.
The invention also provides application of the maleated rosin based saccharide surfactant.
The application of the maleated rosin-based sugar surfactant in the fields of food, daily chemicals, pesticides or medicines is disclosed, wherein the maleated rosin-based sugar surfactant is represented by a formula (1) or is prepared by the preparation method.
The invention has the beneficial effects that:
the maleated rosin based sugar surfactant has the advantages of greenness, easy biodegradation and the like, and can be used in the fields of food, daily chemicals, pesticides or medicines.
Specifically, compared with the prior art, the invention has the following advantages:
the invention combines the maleated rosin with sugar acid (lactone) through diamine connection for the first time to synthesize the novel maleated rosin-based saccharide nonionic surfactant. The raw materials of the maleated rosin and the sugar acid (lactone) are both from natural products, have rich sources and low price, and have the advantages of being renewable, biodegradable and the like. The synthesized maleated rosin-based saccharide nonionic surfactant has the advantages of greenness, easy biodegradation and the like.
The maleated rosin based sugar surfactant has good emulsifying property and foaming property, and can be used in the fields of food, daily chemicals, pesticides or medicines.
Drawings
FIG. 1 is a FT-IR chart of a maleated rosin-based saccharide surfactant obtained in example 1.
Detailed Description
The synthetic route of the maleated rosin-based saccharide surfactant of the invention is as follows:
the present invention will be described in further detail with reference to specific examples in conjunction with the synthesis scheme below. The starting materials, reagents or apparatus used in the examples were obtained from conventional commercial sources unless otherwise specified. Unless otherwise indicated, the testing or testing methods are conventional in the art.
Example 1
Firstly, preparing maleated rosin methyl ester
0.5mol/L of maleated rosin toluene solution is added into a round bottom flask, and then thionyl chloride (molar ratio of thionyl chloride to maleated rosin is 3:1) is added, and the mixture is heated to 80 ℃ in an oil bath for reaction for 3 hours. And after the reaction is finished, spin-drying the solution to obtain the maleated rosin acyl chloride.
Adding a certain amount of methanol into a round-bottom flask, then adding triethylamine (the molar ratio of triethylamine to maleic rosin acyl chloride is 2:1), and finally dropwise adding 0.5mol/L maleic rosin acyl chloride dichloromethane solution. The reaction was carried out at 40 ℃ for 10 h. And after the reaction is finished, spin-drying the solution to obtain the maleic rosin methyl ester.
Secondly, maleic rosin imide MR-DN-n (n is 2, 3 and 4)
A1 mol/L maleic rosin methyl ester ethanol solution is added into a round-bottom flask, and then ethylenediamine (the molar ratio of the ethylenediamine to the maleic rosin methyl ester is 1:1) is added. Heated to 90 ℃ in an oil bath and reacted for 12 h. After the reaction, the solution was spin-dried to obtain maleopimaric acid vinylene (MR-DN-2).
Thirdly, preparing the maleated rosin based sugar surfactant
Adding 0.05mol/L of maleic rosin vinylene amine (MR-DN-2) methanol solution into a round-bottom flask, then adding gluconolactone (the molar ratio of the gluconolactone to the maleic rosin vinylene is 1:1), heating to 60 ℃ in an oil bath, and reacting for 20 hours. And after the reaction is finished, spin-drying the solution to obtain the maleated rosin-based saccharide surfactant (MR-DN-2-GLU).
Example 2
Malathionyldiamine (MR-DN-3) was prepared by substituting ethylenediamine for propylenediamine in the preparation of maleopimarimide according to the preparation method of example 1.
The preparation method of the maleated rosin based sugar surfactant comprises the following steps:
0.1mol/L of maleated rosin acyl imino propylamine (MR-DN-3) methanol solution is added into a round-bottom flask, then gluconic acid (the molar ratio of the gluconic acid to the maleated rosin acyl imino propylamine is 1.2:1) is added, and the mixture is heated to 80 ℃ in an oil bath and reacts for 48 hours. And after the reaction is finished, spin-drying the solution to obtain the maleated rosin-based saccharide surfactant (MR-DN-3-GLU).
Example 3
Referring to the preparation method of example 1, maleic rosin acyl butylamine (MR-DN-4) was prepared by replacing ethylenediamine with butanediamine in the preparation of maleic rosin imide.
The preparation method of the maleated rosin based sugar surfactant comprises the following steps:
10mol/L of maleated rosin acyl butylene imine (MR-DN-4) ethanol solution is added into a round-bottom flask, then lactobionic acid (the molar ratio of lactobionic acid to maleated rosin acyl butylamine is 0.8:1) is added, and the mixture is heated to 90 ℃ in an oil bath and reacted for 72 hours. And after the reaction is finished, spin-drying the solution to obtain the maleated rosin-based saccharide surfactant (MR-DN-4-LAC).
Example 4
The main difference between this example and example 1 lies in the method for preparing the maleated rosin-based saccharide surfactant, which comprises the following steps:
adding 0.01mol/L of maleic rosin vinylene amine (MR-DN-2) methanol solution into a round-bottom flask, then adding gluconolactone (the molar ratio of the gluconolactone to the maleic rosin vinylene is 0.9:1), heating to 80 ℃ in an oil bath, and reacting for 15 h. And after the reaction is finished, spin-drying the solution to obtain the maleated rosin-based saccharide surfactant (MR-DN-2-GLU).
Example 5
The main difference between this example and example 2 is only the method for preparing the maleated rosin-based saccharide surfactant, which specifically comprises the following steps:
6mol/L of maleated rosin acyl imino amine (MR-DN-3) methanol solution is added into a round-bottom flask, then lactobionic acid (the molar ratio of lactobionic acid to maleated rosin acyl imino amine is 1:1) is added, and the mixture is heated to 80 ℃ in an oil bath and reacted for 60 hours. And after the reaction is finished, spin-drying the solution to obtain the maleated rosin-based saccharide surfactant (MR-DN-3-LAC).
Example 6
The main difference between this example and example 3 is only the method for preparing the maleated rosin-based saccharide surfactant, which specifically comprises the following steps:
adding 1mol/L of maleated rosin acyl butylene imine (MR-DN-4) ethanol solution into a round-bottom flask, then adding glucolactone (the molar ratio of the glucolactone to the maleated rosin acyl butylene is 1.1:1), heating to 90 ℃ in an oil bath, and reacting for 10 hours. And after the reaction is finished, spin-drying the solution to obtain the maleated rosin-based saccharide surfactant (MR-DN-4-GLU).
Characterization analysis
And performing FT-IR (Fourier transform infrared) characterization analysis on the prepared maleated rosin-based saccharide surfactant. FT-IR characterization of the samples was performed using the KBr pellet method. FIG. 1 is a FT-IR chart of the maleated rosin-based saccharide surfactant MR-DN-2-GLU prepared in example 1. As can be seen from FIG. 1, 3410cm-1Is the stretching vibration peak of O-H bond in glycosyl of the sample, 1723cm-1The peak is the stretching vibration peak of C ═ O bond in the methyl ester group in the sample, 1767cm-1And 1693cm-1At (b) is the stretching vibration peak of C ═ O bond in imide group in sample, 1538cm-1There is a deformation vibration peak of the N-H bond in the amide group in the sample. The appearance of the characteristic peak indicates that the maleated rosin-based saccharide surfactant is successfully synthesized.
Testing of emulsifying Properties
At room temperature, 40mL of the aqueous solution of the maleated rosin-based saccharide surfactant (MR-DN-2-GLU) prepared in example 1 with the mass fraction of 0.1% and 40mL of benzene were poured into a 100mL stoppered graduated cylinder, plugged, and vigorously shaken 50 times. The time for separating 10mL of benzene was 30 min. This indicates that the sample has better emulsifying properties.
Foam Performance testing
At room temperature, 20mL of the aqueous solution of the maleated rosin-based saccharide surfactant (MR-DN-2-GLU) prepared in example 1 with a mass fraction of 0.1% was added to a 100mL stoppered cylinder, 10mL of water was then added, shaking vigorously for 25 times, and the initial time and the foam height at 5min were recorded. The initial foam height was 77mm and at 5min the foam height was 30 mm. This indicates that the sample has better foam properties.
The maleated rosin based sugar surfactant prepared by the invention has the advantages of greenness, easy biodegradation and the like, has good emulsifying property and foaming property, and can be used in the fields of food, daily chemicals, pesticides or medicines.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A maleated rosin-based saccharide surfactant has a structural formula shown in formula (1):
in the formula (1), n is 2-4; r is glucaric acid group or lactobionic acid group.
2. A preparation method of maleated rosin-based sugar surfactant is characterized by comprising the following steps: the method comprises the following steps:
1) reacting maleated rosin with an acyl chlorination reagent to obtain maleated rosin acyl chloride;
2) reacting maleated rosin acyl chloride with methanol to obtain maleated rosin methyl ester;
3) reacting maleic rosin methyl ester with diamine to obtain maleic rosin imide;
4) reacting maleated rosin imide with sugar acid or sugar acid lactone to obtain the maleated rosin-based saccharide surfactant.
3. The method of claim 2, wherein: in the step 1), the acyl chlorination reagent is selected from at least one of oxalyl chloride and thionyl chloride.
4. The method of claim 2, wherein: in the step 3), the diamine is at least one selected from ethylenediamine, propylenediamine and butylenediamine.
5. The method of claim 2, wherein: in the step 4), the reaction is carried out in an alcohol solvent.
6. The method of claim 5, wherein: in the step 4), the alcohol solvent is at least one selected from methanol and ethanol.
7. The method of claim 6, wherein: in the step 4), the concentration of the maleated rosin imide in the alcohol solvent is 0.01 mol/L-10 mol/L; the molar ratio of the sugar acid or the sugar acid lactone to the maleated rosin imide is (0.8-1.2): 1.
8. the method of claim 7, wherein: in the step 4), the sugar acid is at least one selected from gluconic acid and lactobionic acid; the gluconolactone is gluconolactone.
9. The method of claim 8, wherein: in the step 4), the reaction temperature is 60-90 ℃, and the reaction time is 10-72 h.
10. The application of the maleated rosin based sugar surfactant in the fields of food, daily chemicals, pesticides or medicines is characterized in that: the maleated rosin-based saccharide surfactant is the maleated rosin-based saccharide surfactant of claim 1, or is prepared by the preparation method of any one of claims 2 to 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911302963.6A CN111111552B (en) | 2019-12-17 | 2019-12-17 | Malathion-based saccharide surfactant and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911302963.6A CN111111552B (en) | 2019-12-17 | 2019-12-17 | Malathion-based saccharide surfactant and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111111552A true CN111111552A (en) | 2020-05-08 |
| CN111111552B CN111111552B (en) | 2022-01-11 |
Family
ID=70499340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911302963.6A Active CN111111552B (en) | 2019-12-17 | 2019-12-17 | Malathion-based saccharide surfactant and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111111552B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113621443A (en) * | 2021-09-10 | 2021-11-09 | 福建省佑达环保材料有限公司 | Composition for cleaning semiconductor chip solid wax |
| CN119684514A (en) * | 2024-12-09 | 2025-03-25 | 广西民族大学 | Preparation method and application of maleated rosin-based hydrogel |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1648127A (en) * | 2004-01-19 | 2005-08-03 | 北京师范大学 | N-Hydroxymaleopimaric acid imide sulfonate photoacid generator and its synthesis method |
| CN1803820A (en) * | 2005-11-30 | 2006-07-19 | 中国林业科学研究院林产化学工业研究所 | Palmic acid glucoside and preparation method thereof |
| CN101638474A (en) * | 2009-09-02 | 2010-02-03 | 中国科学院长春应用化学研究所 | Maleated rosin acyl imino amines epoxy hardener for powder coating and preparation method thereof |
| US20110303376A1 (en) * | 2010-06-15 | 2011-12-15 | Plasmine Technology, Inc. | Imidized and amidized rosin compositions for paper sizes and other applications |
| CN102558289A (en) * | 2011-12-21 | 2012-07-11 | 东莞市信诺橡塑工业有限公司 | The synthetic method of gum rosin derivative |
| CN102898484A (en) * | 2012-10-26 | 2013-01-30 | 广西民族大学 | Rosin modified alkali lignin sulfonate and preparation method of rosin modified alkali lignin sulfonate |
| US8568760B2 (en) * | 2009-12-30 | 2013-10-29 | Surmodics, Inc. | Hydrophobic polysaccharides with pendent groups having terminal reactive functionalities and medical uses thereof |
-
2019
- 2019-12-17 CN CN201911302963.6A patent/CN111111552B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1648127A (en) * | 2004-01-19 | 2005-08-03 | 北京师范大学 | N-Hydroxymaleopimaric acid imide sulfonate photoacid generator and its synthesis method |
| CN1803820A (en) * | 2005-11-30 | 2006-07-19 | 中国林业科学研究院林产化学工业研究所 | Palmic acid glucoside and preparation method thereof |
| CN101638474A (en) * | 2009-09-02 | 2010-02-03 | 中国科学院长春应用化学研究所 | Maleated rosin acyl imino amines epoxy hardener for powder coating and preparation method thereof |
| US8568760B2 (en) * | 2009-12-30 | 2013-10-29 | Surmodics, Inc. | Hydrophobic polysaccharides with pendent groups having terminal reactive functionalities and medical uses thereof |
| US20110303376A1 (en) * | 2010-06-15 | 2011-12-15 | Plasmine Technology, Inc. | Imidized and amidized rosin compositions for paper sizes and other applications |
| CN102558289A (en) * | 2011-12-21 | 2012-07-11 | 东莞市信诺橡塑工业有限公司 | The synthetic method of gum rosin derivative |
| CN102898484A (en) * | 2012-10-26 | 2013-01-30 | 广西民族大学 | Rosin modified alkali lignin sulfonate and preparation method of rosin modified alkali lignin sulfonate |
Non-Patent Citations (1)
| Title |
|---|
| 周文富 等: "松香系列非离子表面活性剂的合成与应用", 《林产化工通讯》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113621443A (en) * | 2021-09-10 | 2021-11-09 | 福建省佑达环保材料有限公司 | Composition for cleaning semiconductor chip solid wax |
| CN119684514A (en) * | 2024-12-09 | 2025-03-25 | 广西民族大学 | Preparation method and application of maleated rosin-based hydrogel |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111111552B (en) | 2022-01-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111111552B (en) | Malathion-based saccharide surfactant and preparation method and application thereof | |
| CN108997520A (en) | A kind of norbornene derivative sugar unit containing foreign peoples homopolymer and its synthetic method | |
| CN110964081B (en) | Alkyl maleimide sodium carboxylate and preparation method and application thereof | |
| CN115353679B (en) | High-strength polyethylene wax-montmorillonite modified polyethylene material and preparation method thereof | |
| CN115368915B (en) | A quaternary ammonium salt sodium carboxylate sulfonic acid surfactant and its preparation method and application | |
| CN120329532B (en) | Bio-based polycarbonate and preparation method thereof | |
| CN111111551A (en) | Rosin glycosyl amide surfactant and preparation method and application thereof | |
| CN111111549A (en) | Dehydroabietyl-based saccharide surfactant and preparation method and application thereof | |
| CN105732442B (en) | Oligomeric-type surfactant, its preparation method and application | |
| US9556282B2 (en) | Modified cellulose and composite material using the same | |
| CN116217510B (en) | A rosin-based polymer with high hydrogen bonding force, preparation method thereof and application thereof | |
| CN111118236A (en) | A kind of fatliquoring agent intermediate and preparation method thereof | |
| CN115232274B (en) | Benzoxazine oligomer toughening agent based on long aliphatic chain phenol and its preparation method and application | |
| CN110016133B (en) | Macromolecular nucleating agent for rapid crystallization of polylactic acid and use method thereof | |
| CN115386011B (en) | A kind of preparation method of cyanoethyl cellulose | |
| CN110563698A (en) | Novel protein cross-linking agent and preparation method thereof | |
| CN111118237B (en) | Light-resistant fatting agent intermediate | |
| CN116515084A (en) | Bio-basic-characteristic flame-retardant self-curing epoxy monomer, preparation method thereof and epoxy resin prepared from same | |
| CN101735287B (en) | Method for preparing 2, 3, 4, 6-tetraacylglucopyranose | |
| CN113214332A (en) | Water-soluble compound based on naringin and preparation method thereof | |
| CN119161288B (en) | A sodium pyrrolidone sulfonate surfactant and its preparation method and application | |
| CN112517061A (en) | Sulfonic acid type solid acid catalyst and preparation method thereof | |
| CN117105819B (en) | Preparation method of intermediate of irbesartan isomer | |
| Li et al. | Etherifying modification of xylan-type hemicellulose and its characterization | |
| CN113121729B (en) | Preparation method of polyvinyl chloride modified by saccharic (aldehydic) acid, polyvinyl chloride and application |
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 | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 510665 Guangzhou, Guangdong, Tianhe District Province Road West, No. 318 Patentee after: Institute of chemical engineering, Guangdong Academy of Sciences Patentee after: GUANGDONG JINBAI CHEMICAL Co.,Ltd. Address before: 510665 Guangzhou, Guangdong, Tianhe District Province Road West, No. 318 Patentee before: GUANGDONG RESEARCH INSTITITUTE OF PETROCHEMICAL AND FINE CHEMICAL ENGINEERING Patentee before: GUANGDONG JINBAI CHEMICAL Co.,Ltd. |
|
| CP01 | Change in the name or title of a patent holder |