CN111154109A - Synthesis method of novel response type amino modified polyether organic silicon surfactant - Google Patents
Synthesis method of novel response type amino modified polyether organic silicon surfactant Download PDFInfo
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- CN111154109A CN111154109A CN202010011468.6A CN202010011468A CN111154109A CN 111154109 A CN111154109 A CN 111154109A CN 202010011468 A CN202010011468 A CN 202010011468A CN 111154109 A CN111154109 A CN 111154109A
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- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 29
- 229920000570 polyether Polymers 0.000 title claims abstract description 29
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 28
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 18
- 239000010703 silicon Substances 0.000 title claims abstract description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims abstract description 14
- 230000004044 response Effects 0.000 title claims abstract description 12
- 238000001308 synthesis method Methods 0.000 title claims abstract description 9
- 229920002545 silicone oil Polymers 0.000 claims abstract description 22
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000004593 Epoxy Substances 0.000 claims abstract description 9
- -1 polyoxyethylene acetate Polymers 0.000 claims abstract description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000003381 stabilizer Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 3
- 238000000967 suction filtration Methods 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 229940126062 Compound A Drugs 0.000 claims description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 238000005316 response function Methods 0.000 claims 1
- 238000006459 hydrosilylation reaction Methods 0.000 abstract description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
- 230000002776 aggregation Effects 0.000 description 7
- 238000004220 aggregation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000002296 dynamic light scattering Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000000638 stimulation Effects 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000004043 responsiveness Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 229920000881 Modified starch Polymers 0.000 description 2
- 239000004368 Modified starch Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 235000019426 modified starch Nutrition 0.000 description 2
- 230000010494 opalescence Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000012637 gene transfection Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004754 hydrosilicons Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention discloses a synthesis method of a novel amino modified polyether organic silicon surfactant with response, which comprises the following steps: sequentially adding quantitative high-hydrogen-content silicone oil, D4, MM, concentrated sulfuric acid and the like into a reactor, starting a stirrer, heating to 50-60 ℃, adjusting the pH of a product to 7.0 by using soda ash after the required viscosity is reached, and performing suction filtration by using a filter flask to obtain colorless and transparent low-hydrogen-content silicone oil; taking a certain amount of PHMS, allyl glycidyl ether and an epoxy stabilizer, sequentially adding into a reactor, and introducing N2Protecting, starting a stirrer, raising the temperature to 80 ℃, reacting for 1h at a constant temperature of 90 ℃, then adding allyl polyoxyethylene acetate and chloroplatinic acid into the reactor, and reacting until the mixture is transparent. Introducing allyl polyoxyethylene acetate and allyl glycidyl ether to polysiloxane chain of hydrogen-containing silicone oil through hydrosilylation reaction to prepare modified polyether organosilicon intermediate, polyoxyThe introduction of ethylene increases the hydrophilicity.
Description
Technical Field
The invention relates to a synthetic method of a surfactant, in particular to a synthetic method of a novel amino modified polyether organic silicon surfactant with response.
Background
The aggregation structure from micrometer scale to nanometer scale is rich, so that the surfactant has important position in many fields of material science, nanometer science, biological medicine and the like. Therefore, the regulation of surfactant aggregation behavior is becoming the focus of current research. If a group with stimulus responsiveness is introduced into the structure of the surfactant, the surfactant responds to external stimulus by changing external factors, so that the development of the novel surfactant has potential value, such as: develops a new separation method, a gene transfection agent and the controllable release of a carrier drug. Wherein the high molecular surfactant has some characteristics that the low molecular surfactant does not have, such as: good thickening power, emulsifying power, dispersibility and low toxicity. The polyether modified organosilicon surfactant can combine the advantages of organosilicon and polyether, the organosilicon has the characteristics of no toxicity, high temperature resistance, surface tension reduction, good stability and the like, and the polyether chain segment can improve the water solubility of the polymer and has the characteristics of low glass transition temperature, good adaptability, acid and alkali resistance, biocompatibility and the like. In order to better improve the water solubility of the polyether silicone oil, an amino chain is grafted at the end of the silicone oil chain, so that the polyether silicone oil has a plurality of special properties besides the properties of common nonionic surfactants. Besides good water solubility and low surface tension, the modified starch has excellent surface activity such as biocompatibility, solubilization, defoaming property and the like, so that the modified starch is widely applied to various application fields such as leather finishing, textile softening, foam homogenizing and defoaming, wetting and leveling, personal care and the like. However, the domestic polyether modified silicone oil is still different from the imported modified silicone oil, so people pay more attention to the development and application of the modified polyether silicone oil in recent years.
Disclosure of Invention
The invention aims to provide a synthesis method of a novel amino modified polyether organic silicon surfactant with response, the method has the advantages that the surface activity is improved and the aggregation behavior is rich due to the introduction of amine into a hydrophilic head group, and the aggregation has pH and concentration stimulation responsiveness, so that the potential application of the surfactant is further expanded. Meanwhile, the introduction of amino groups enables the modified surfactant to have better biodegradability and is beneficial to environmental protection.
In order to achieve the purpose, the invention adopts the following technical scheme:
the response type amino modified polyether organic silicon surfactant is a compound shown as the following formula A:
a synthesis method of a novel amino modified polyether organic silicon surfactant with response type comprises the following steps:
1) synthesis of low hydrogen-containing silicone oil
Sequentially adding quantitative high-hydrogen-content silicone oil, D4, MM, concentrated sulfuric acid and the like into a reactor, starting a stirrer, heating to 50-60 ℃, reacting for a period of time, adjusting the pH of a product to 7.0 by using sodium carbonate after the required viscosity is reached, and then performing suction filtration by using a filter flask to obtain colorless and transparent low-hydrogen-content silicone oil;
the method for synthesizing the low PHMS (namely the low hydrogen silicone oil) is multiple, most reaction processes are not easy to control, the requirements on the specialty of laboratory operators and instruments are very high, and the method is not suitable for common laboratories, but the high PHMS telomerization method has mild reaction conditions and simple preparation process, so the low PHMS required by the experimental grafting reaction is prepared by the telomerization method.
2) Preparation of polyether and allyl glycidyl ether co-modified organic silicon
Taking a certain amount of PHMS, allyl glycidyl ether and an epoxy stabilizer, sequentially adding into a reactor, and introducing N2Protecting, starting a stirrer, raising the temperature to 80 ℃, adding chloroplatinic acid, reacting for 1 hour at a constant temperature of 90 ℃, then adding allyl polyoxyethylene acetate and chloroplatinic acid into the reactor, and reacting to be transparent at a temperature of 90-100 ℃.
By hydrosilylation, allyl polyoxyethylene acetate and allyl glycidyl ether are introduced to a polysiloxane chain of hydrogen-containing silicone oil to prepare a modified polyether organic silicon intermediate, and the introduction of polyoxyethylene increases hydrophilicity. Meanwhile, the side reaction of hydroxyl terminated by polyoxyalkane and silicone oil in the hydrosilylation process is effectively reduced, the conversion rate is improved, and the final synthetic product is easy to spread on an interface, high in branching degree and in a space network structure.
3) Synthesis of amino modified polyether organic silicon
Adding a certain amount of acetone and isopropanol into a reactor filled with epoxy polyether modified silicone oil as a stabilizer, adding a certain proportion of diethylamine, and adding N2Heating in water under protection, controlling the temperature at 80 ℃, stirring and reacting for 10 hours, removing low-boiling-point substances by low-pressure distillation after the reaction is finished, and finally filtering the reaction product by diatomite to obtain the compound A.
3. In the step 2), the mass ratio of PHMS to allyl glycidyl ether to epoxy stabilizer to chloroplatinic acid to allyl polyoxyethylene polyoxypropylene alcohol is 100:32:1-4:2-6: 20.
3. The synthesis method of the response type amino modified polyether organic silicon surfactant as claimed in claim 1, wherein the mass ratio of the epoxy polyether modified silicone oil, the acetone, the isopropanol and the diethylamine in the step 3) is 61-78:120:50-70: 3-9.
The modified polyether organic silicon intermediate is added with diethylamine in a certain proportion to increase the hydrophilicity, and simultaneously, a stimulation response type group is introduced, so that an aggregate can be formed in a solution, and a stimulation response system is realized.
After the compound A is refined and purified, infrared spectrum analysis is carried out, and the wave number data of each functional group is O-H (3479 CM)-1): stretching vibration peak C-H of hydroxyl group (2960, 2969 CM)-1) (ii) a Stretching vibration peak Si-O-Si of C-H bond in hydrosilation map (1098,1030CM-1) (ii) a Peak of bending vibration of silicon-oxygen bond Si-CH3(1454,1260,801 CM)-1): the stretching and bending vibration peaks of the silylmethyl groups on the siloxane disappeared from the Si-H (2127.54), the most important characteristic peak of the hydrosilicon in the modified silicone silicon spectrum, indicating that the addition reaction had indeed proceeded according to our experimental design.
The invention has the beneficial effects that:
the introduction of amine in the hydrophilic head group improves the surface activity and has rich aggregation behavior, and the aggregate has pH and concentration stimulation responsiveness, thereby further expanding the potential application of the aggregate. Meanwhile, the introduction of amino groups enables the modified surfactant to have better biodegradability and is beneficial to environmental protection.
Drawings
FIG. 1 shows DLS results for aqueous solutions of Compound A at various pH conditions.
Detailed description of the preferred embodiments
Example 1
Due to the existence of amine groups in the hydrophilic head group of the surfactant, the compound A can combine protons in the solution, and the surfactant has two existing forms of cations and anions in the solution along with the change of the pH value of the solution. Due to the differences in charge repulsion between the two forms of head groups and the hydrophilic capacity of the head groups, the corresponding parameters of compound a are also significantly different. Thus, as the pH in the solution changes, the morphology of the aggregates may also change. In combination with the intuitive phenomenon of different pH's of their surfactants at the same mass concentration, we can initially speculate on the transition of their aggregates. As the pH of the solution increased, the sample transitioned from a colorless transparent solution to a solution with blue opalescence, presumably with large self-assemblies. The compound a solution has the property of pH-induced transition of aggregation behavior.
According to the microscopic phenomenon, surfactant solutions with the same concentration and different pH values are prepared, ultrasonic dispersion is carried out for 30min, Dynamic Light Scattering (DLS) of the surfactant aqueous solutions with the same concentration and different pH values is measured by using a Nano-ZS dynamic laser light scattering instrument, and the transition of the aggregation behavior of the compound A is deeply researched.
0.5g/L of compound A solution under the same concentration and different pH conditions is prepared respectively, and the particle size of the aggregate is characterized by DLS, as shown in figure 1. At a pH of 3.0, the solution is colorless and transparent, and the aggregate particle size distribution of the solution is a monomodal distribution of several nanometers to more than ten nanometers, and spherical micelles are adopted; when the pH value is 6.0, the solution is slightly bluish opalescent, the particle size distribution of the aggregates in the solution is single peak in the range of tens of nanometers, and the aggregates in the solution are rod-shaped or worm-shaped; when the pH of the solution is continuously increased to 10.0, the turbidity of the solution is increased, the particle size distribution of solution aggregates is a single peak from hundreds of nanometers to thousands of nanometers, the solution is blue opalescence, and the aggregate structure of the solution is supposed to be a vesicle.
The above-described embodiments are intended to illustrate the substance of the present invention, but are not intended to limit the scope of the present invention. It will be understood by those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof without departing from the true spirit and scope of the invention.
Claims (3)
1. A synthesis method of a novel response type amino modified polyether organic silicon surfactant is characterized by comprising the following steps:
1) synthesis of low hydrogen-containing silicone oil
Mixing the components in a molar ratio of 1-2: 5: 1-4 of high hydrogen-containing silicone oil, D4, MM and concentrated sulfuric acid are sequentially put into a reactor, a stirrer is started, the temperature is increased to 50-60 ℃, after reaction for a period of time, the pH of a product is adjusted to 7.0 by using sodium carbonate, and then suction filtration is carried out by using a filter flask to obtain colorless and transparent low hydrogen-containing silicone oil;
2) preparation of polyether and allyl glycidyl ether co-modified organic silicon
Taking a certain amount of PHMS, allyl glycidyl ether and an epoxy stabilizer, sequentially adding into a reactor, introducing N2 for protection, starting a stirrer, raising the temperature to 80 ℃, reacting for 1h at a constant temperature of 90 ℃, then adding allyl polyoxyethylene acetate and chloroplatinic acid into the reactor, and reacting to be transparent at a temperature of 90-100 ℃;
3) synthesis of amino modified polyether organic silicon
Adding a certain amount of acetone and isopropanol into a reactor filled with epoxy polyether modified silicone oil as a stabilizer, adding a certain proportion of diethylamine, and adding N2Heating in water under protection, controlling the temperature at 80 ℃, stirring and reacting for 10 hours, removing low-boiling-point substances by low-pressure distillation after the reaction is finished, and finally filtering the reaction product by diatomite to obtain the compound A.
2. The synthesis method of the novel amino modified polyether organic silicon surfactant with response function according to claim 1, wherein the mass ratio of PHMS, allyl glycidyl ether, epoxy stabilizer, chloroplatinic acid and allyl polyoxyethylene polyoxypropylene alcohol in the step 2) is 100:32:1-4:2-6: 20.
3. The synthesis method of the novel amino modified polyether organic silicon surfactant with response property according to claim 1 is characterized in that the mass ratio of the epoxy polyether modified silicone oil, the acetone, the isopropanol and the diethylamine in the step 3) is 61-78:120:50-70: 3-9.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115010933A (en) * | 2022-06-14 | 2022-09-06 | 武汉三源特种建材有限责任公司 | Six-carbon foam stabilizing water reducer and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115010933A (en) * | 2022-06-14 | 2022-09-06 | 武汉三源特种建材有限责任公司 | Six-carbon foam stabilizing water reducer and preparation method thereof |
| CN115010933B (en) * | 2022-06-14 | 2023-09-12 | 武汉三源特种建材有限责任公司 | Six-carbon foam-stabilizing type water reducer and preparation method thereof |
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Application publication date: 20200515 |