CN111004274A - Cyclosiloxane modified glutamic acid and preparation method thereof - Google Patents
Cyclosiloxane modified glutamic acid and preparation method thereof Download PDFInfo
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- CN111004274A CN111004274A CN201911225529.2A CN201911225529A CN111004274A CN 111004274 A CN111004274 A CN 111004274A CN 201911225529 A CN201911225529 A CN 201911225529A CN 111004274 A CN111004274 A CN 111004274A
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- glutamic acid
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- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 20
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 235000013922 glutamic acid Nutrition 0.000 claims abstract description 15
- 239000004220 glutamic acid Substances 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 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 11
- SNYNNFDVNITLRQ-UHFFFAOYSA-N 2,2,4,4,6,6,8-heptamethyl-1,3,5,7,2,4,6,8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 SNYNNFDVNITLRQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000693 micelle Substances 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical class OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 34
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000003472 neutralizing effect Effects 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 229930195712 glutamate Natural products 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- -1 alkane modified glutamic acid Chemical class 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- AVBJHQDHVYGQLS-AWEZNQCLSA-N (2s)-2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-AWEZNQCLSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- HWUINYGRRJTXGE-UTLKBRERSA-L disodium;(2s)-2-(dodecanoylamino)pentanedioate Chemical compound [Na+].[Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC([O-])=O HWUINYGRRJTXGE-UTLKBRERSA-L 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Abstract
The invention discloses cyclosiloxane modified glutamic acid and a preparation method thereof, which comprises the following steps: adding a sodium hydroxide solution into a glutamic acid aqueous solution for neutralization under stirring, dropwise adding allyl glycidyl ether into a reaction system after the neutralization is finished, continuing to react for a certain time after the dropwise adding is finished, and distilling the obtained solution under reduced pressure to remove water after the reaction is finished to obtain 2-hydroxy-3-allyloxy glutamic acid disodium salt; adding the 2-hydroxy-3-allyloxy glutamic acid disodium salt, heptamethylcyclotetrasiloxane and a catalyst into a reaction kettle, reacting in the presence of a low-carbon alcohol solvent, and evaporating the low-carbon alcohol solvent after the reaction is finished to obtain the modified glutamic acid. The cyclosiloxane modified glutamic acid provided by the invention has higher surface activity than the existing alkane modified glutamic acid as a new modified glutamic acid, and the process is simple and not troublesome, and the cost is low.
Description
Technical Field
The invention belongs to the technical field of chemistry and chemical engineering, and particularly relates to cyclosiloxane modified glutamic acid and a preparation method thereof.
Background
Glutamic acid is the amino acid with the largest yield in the world, and is widely applied to the fields of food, medical treatment, cosmetics and the like due to good performances of enhancing freshness, nourishing, improving intelligence development and the like. The glutamic acid has good hydrophilicity and can be used for synthesizing a surfactant, at present, the N-fatty acyl glutamic acid surfactant is mainly synthesized, the used hydrophobic chain is alkane, and the modification of the glutamic acid by using cyclosiloxane is not reported.
Because the organosilicon surfactant has the characteristics of low surface tension, good spreading, wettability, thermal stability and the like, the organosilicon surfactant is widely applied to the fields of polyurethane foam products, textiles, paints and coatings, cosmetics and pesticides. Silicone surfactants can be classified into trisiloxane, comb, ABA block, and ring structures according to their molecular structure.
The existing prepared modified glutamic acid is mainly modified by alkane, and the surface tension of the modified glutamic acid is more than 30mN/m, so that the application range of the modified glutamic acid is influenced, and the modified glutamic acid with high surface activity needs to be developed.
Disclosure of Invention
The invention aims to provide cyclosiloxane modified glutamic acid with higher surface activity than the existing alkane modified glutamic acid.
Another task of the invention is to provide a preparation method of cyclosiloxane modified glutamic acid.
In order to realize the purpose of the invention, the invention provides the following specific technical scheme: the cyclosiloxane modified glutamic acid has the following structural formula:
in one embodiment of the invention, the aqueous solution of the cyclosiloxane-modified glutamic acid has a minimum surface tension of 29 mN/m; the critical micelle concentration in the aqueous solution was 350 mg/L.
In order to realize another purpose of the invention, the technical scheme provided by the invention is as follows: a preparation method of cyclosiloxane modified glutamic acid comprises the following steps:
(1) preparation of 2-hydroxy-3-allyloxy glutamic acid disodium salt
Weighing glutamic acid into a reaction kettle, adding deionized water for dissolving, adding a sodium hydroxide solution for neutralization under stirring, dropwise adding allyl glycidyl ether into a reaction system at a certain temperature after neutralization is finished, continuing to react for a certain time after dropwise adding, and distilling the obtained solution under reduced pressure to remove water after the reaction is finished to obtain 2-hydroxy-3-allyloxy glutamic acid disodium salt;
(2) preparation of cyclosiloxane-modified glutamic acid
Adding the 2-hydroxy-3-allyloxy glutamic acid disodium salt obtained in the step (1), heptamethylcyclotetrasiloxane and a catalyst into a reaction kettle, reacting in the presence of a low-carbon alcohol solvent, controlling the reaction temperature and the reaction time in the presence of the low-carbon alcohol solvent, and evaporating the low-carbon alcohol solvent after the reaction is finished to obtain the cyclosiloxane modified glutamic acid.
In a preferred embodiment of the present invention, in the step (1), the molar ratio of glutamic acid to sodium hydroxide and allyl glycidyl ether is 1:2: 1; controlling the reaction temperature to be 20-80 ℃; the dropping time is controlled to be 0.5-4 h, and the reaction time after dropping is controlled to be 1-20 h.
In a preferred embodiment of the present invention, in the step (1), the sodium hydroxide solution has a mass concentration of 10 to 40%.
In a preferred mode of the present invention, in the step (2), the molar ratio of the disodium salt of 2-hydroxy-3-allyloxy glutamic acid to heptamethylcyclotetrasiloxane is 1: controlling the reaction temperature and the reaction time in the presence of a low-carbon alcohol solvent, namely controlling the reaction temperature to be the reflux temperature of the low-carbon alcohol solvent, and controlling the reaction time to be 1-40 h; the low-carbon alcohol solvent is any one of methanol, ethanol, propanol or isopropanol.
In a preferred embodiment of the present invention, in the step (2), the catalyst is a platinum catalyst, specifically, the platinum catalyst is one or more of chloroplatinic acid and kastedt (Karstedt), and the mass content of the catalyst in the reaction raw materials (i.e., 2-hydroxy-3-allyloxy glutamic acid disodium salt and heptamethylcyclotetrasiloxane) is 0.002% -0.01%.
Compared with the prior art, the cyclosiloxane modified glutamic acid provided by the invention has higher surface activity as a new modified glutamic acid compared with the existing alkane modified glutamic acid. The preparation process is simple and not troublesome, and the preparation cost is low, so that the preparation method can meet the requirement of industrial scale-up production and can ensure that the obtained cyclosiloxane modified glutamic acid has excellent surface activity, thereby being applied to the fields of cosmetics, biotechnology, medicine and the like.
Detailed Description
The above-described scheme is further illustrated below with reference to specific examples. It is to be understood that these examples are for illustrative purposes and are not intended to limit the scope of the present invention, and that equivalent changes and modifications made in accordance with the spirit of the present invention are intended to be included within the scope of the present invention. The conditions used in the examples may be further adjusted according to specific conditions, and the conditions used in the experiments are not specifically mentioned.
Example 1
(1) Preparation of 2-hydroxy-3-allyloxy glutamic acid disodium salt
Adding 14.7Kg (100mol) of glutamic acid, 40Kg (200mol) of sodium hydroxide solution with the concentration of 20% and 30Kg of deionized water into a reaction kettle, stirring and neutralizing to obtain glutamic acid disodium salt, weighing 11.4Kg (100mol) of allyl glycidyl ether, dropwise adding the mixture into the reaction kettle at 20 ℃ for 2h, continuing to react for 20h after dropwise adding, and after the reaction is finished, carrying out reduced pressure distillation to remove water to obtain 30.2Kg (99mol) of 2-hydroxy-3-allyloxy glutamic acid disodium salt.
(2) Preparation of cyclosiloxane-modified glutamic acid
15.25Kg (50mol) of the disodium 2-hydroxy-3-allyloxy glutamate, 14.1Kg (50mol) of heptamethylcyclotetrasiloxane and 0.58g of chloroplatinic acid catalyst were charged into a reaction vessel, and reacted at reflux temperature for 1 hour with methanol as a solvent, and the solvent methanol was distilled off to obtain 29.05Kg (49.5mol) of cyclosiloxane-modified glutamic acid.
The minimum surface tension of the aqueous solution was 29mN/m and the critical micelle concentration was 350mg/L as measured by a K12 surface tensiometer.
Example 2
(1) Preparation of 2-hydroxy-3-allyloxy glutamic acid disodium salt
Adding 14.7Kg (100mol) of glutamic acid, 80Kg (200mol) of 10% sodium hydroxide solution and 20Kg of deionized water into a reaction kettle, stirring and neutralizing to obtain glutamic acid disodium salt, weighing 11.4Kg (100mol) of allyl glycidyl ether, dropwise adding the allyl glycidyl ether into the reaction kettle at 80 ℃ for 0.5h, continuing to react for 10h after dropwise adding, and after the reaction is finished, carrying out reduced pressure distillation to remove water to obtain 29.6Kg (97mol) of 2-hydroxy-3-allyloxy glutamic acid disodium salt.
(2) Preparation of cyclosiloxane-modified glutamic acid
15.25Kg (50mol) of the disodium 2-hydroxy-3-allyloxy glutamate, 14.1Kg (50mol) of heptamethylcyclotetrasiloxane and 1.17g of chloroplatinic acid catalyst were charged into a reaction vessel, and reacted at reflux temperature for 40 hours with ethanol as a solvent, and the solvent ethanol was distilled off to obtain 28.76Kg (49mol) of cyclosiloxane-modified glutamic acid.
The minimum surface tension of the aqueous solution was 29mN/m and the critical micelle concentration was 350mg/L as measured by a K12 surface tensiometer.
Example 3
(1) Preparation of 2-hydroxy-3-allyloxy glutamic acid disodium salt
Adding 14.7Kg (100mol) of glutamic acid, 20Kg (100mol) of 40% sodium hydroxide solution and 20Kg of deionized water into a reaction kettle, stirring and neutralizing to obtain glutamic acid disodium salt, weighing 11.4Kg (100mol) of allyl glycidyl ether, dropwise adding into the reaction kettle at 40 ℃ for 4h, continuing to react for 5h after dropwise adding, and after the reaction is finished, carrying out reduced pressure distillation to remove water to obtain 28.9Kg (95mol) of 2-hydroxy-3-allyloxy glutamic acid disodium salt.
(2) Preparation of cyclosiloxane-modified glutamic acid
15.25Kg (50mol) of the disodium 2-hydroxy-3-allyloxy glutamate, 14.1Kg (50mol) of heptamethylcyclotetrasiloxane, and 2.93g of Karstedt's catalyst were charged into a reaction vessel, and reacted at reflux temperature for 10 hours using propanol as a solvent, and the solvent propanol was distilled off to obtain 27.60Kg (47mol) of cyclosiloxane-modified glutamic acid.
The minimum surface tension of the aqueous solution was 29mN/m and the critical micelle concentration was 350mg/L as measured by a K12 surface tensiometer.
Example 4
(1) Preparation of 2-hydroxy-3-allyloxy glutamic acid disodium salt
Adding 14.7Kg (100mol) of glutamic acid, 26.6Kg (100mol) of 30% sodium hydroxide solution and 30Kg of deionized water into a reaction kettle, stirring and neutralizing to obtain glutamic acid disodium salt, weighing 11.4Kg (100mol) of allyl glycidyl ether, dropwise adding into the reaction kettle at 50 ℃ for 3h, continuing to react for 7h after dropwise adding, and after the reaction is finished, carrying out reduced pressure distillation to remove water to obtain 28.9Kg (95mol) of 2-hydroxy-3-allyloxy glutamic acid disodium salt.
(2) Preparation of cyclosiloxane-modified glutamic acid
18.1Kg (50mol) of the disodium 2-hydroxy-3-allyloxy glutamate, 14.1Kg (50mol) of heptamethylcyclotetrasiloxane and 1.47g of Karstedt's catalyst were charged into a reaction vessel, and reacted at reflux temperature for 20 hours with isopropanol as a solvent, and the solvent isopropanol was distilled off to obtain 26.70Kg (45.5mol) of cyclosiloxane-modified glutamic acid.
The minimum surface tension of the aqueous solution was 29mN/m and the critical micelle concentration was 350mg/L as measured by a K12 surface tensiometer.
Comparative examples
(1) Preparation of lauroyl glutamic acid
Adding 14.7Kg (100mol) of glutamic acid, 26.6Kg (100mol) of sodium hydroxide solution with the concentration of 30% and 30Kg of deionized water into a reaction kettle, stirring and neutralizing to obtain glutamic acid disodium salt, weighing 21.8Kg (100mol) of lauroyl chloride, dropwise adding into the reaction kettle at the temperature of 10-15 ℃ for 5 hours, and continuing to react for 2 hours after dropwise adding; after the reaction, the water was removed by distillation under reduced pressure to obtain 35.3Kg (95mol) of lauroyl glutamic acid disodium salt
The minimum surface tension of the aqueous solution was 32mN/m and the critical micelle concentration was 640mg/L as measured by a K12 surface tensiometer.
Claims (10)
1. The cyclosiloxane modified glutamic acid is characterized by having a structural formula as follows:
2. the modified glutamic acid of claim 1, wherein an aqueous solution of the modified glutamic acid has a minimum surface tension of 29mN/m and a critical micelle concentration of 350mg/L in the aqueous solution.
3. The preparation method of cyclosiloxane modified glutamic acid is characterized by comprising the following steps:
(1) adding a sodium hydroxide solution into a glutamic acid solution for neutralization under stirring, dropwise adding allyl glycidyl ether into a reaction system after the neutralization is finished, continuing to react for a certain time after the dropwise adding is finished, and distilling the obtained solution under reduced pressure to remove water after the reaction is finished to obtain 2-hydroxy-3-allyloxy glutamic acid disodium salt;
(2) adding the 2-hydroxy-3-allyloxy glutamic acid disodium salt, heptamethylcyclotetrasiloxane and a catalyst into a reaction kettle, reacting in the presence of a low-carbon alcohol solvent, and evaporating the low-carbon alcohol solvent after the reaction is finished to obtain the modified glutamic acid.
4. The method of claim 3, wherein the molar ratio of glutamic acid to sodium hydroxide to allyl glycidyl ether is 1:2: 1.
5. The method of claim 3, wherein the allyl glycidyl ether is added dropwise into the reaction system at 20-80 ℃ for 0.5-4 h, and the reaction is continued for 1-20 h after the addition.
6. The method according to claim 3, wherein the sodium hydroxide solution has a mass concentration of 10 to 40%.
7. The method of claim 3, wherein the molar ratio of 2-hydroxy-3-allyloxy glutamic acid disodium salt to heptamethylcyclotetrasiloxane is 1: 1.
8. the method of claim 3, wherein the reaction is carried out for 1-40 h at a reflux temperature in the presence of a low-carbon alcohol solvent; the low-carbon alcohol solvent is any one of methanol, ethanol, propanol or isopropanol.
9. The method of claim 3, wherein the catalyst is a platinum-based catalyst; the mass content of the catalyst in the reaction raw material is 0.002% -0.01%.
10. The method of claim 3 or 9, wherein the catalyst is one or more of chloroplatinic acid or kast.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113181828A (en) * | 2021-03-18 | 2021-07-30 | 广东雷邦高新材料有限公司 | Environment-friendly amino acid modified organic silicon surfactant and preparation method thereof |
| CN114656498A (en) * | 2022-03-29 | 2022-06-24 | 常熟理工学院 | Organic silicon modified sarcosine and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52114699A (en) * | 1976-03-22 | 1977-09-26 | Toshiba Silicone Co Ltd | Preparation of silicones modified with amino acids |
| CN106311075A (en) * | 2016-08-15 | 2017-01-11 | 常熟理工学院 | Cyclosiloxane surfactant and preparation method thereof |
| CN107698615A (en) * | 2017-09-13 | 2018-02-16 | 常熟理工学院 | A kind of amino-acid modified tetrasiloxane surfactant and preparation method thereof |
-
2019
- 2019-12-04 CN CN201911225529.2A patent/CN111004274A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52114699A (en) * | 1976-03-22 | 1977-09-26 | Toshiba Silicone Co Ltd | Preparation of silicones modified with amino acids |
| CN106311075A (en) * | 2016-08-15 | 2017-01-11 | 常熟理工学院 | Cyclosiloxane surfactant and preparation method thereof |
| CN107698615A (en) * | 2017-09-13 | 2018-02-16 | 常熟理工学院 | A kind of amino-acid modified tetrasiloxane surfactant and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113181828A (en) * | 2021-03-18 | 2021-07-30 | 广东雷邦高新材料有限公司 | Environment-friendly amino acid modified organic silicon surfactant and preparation method thereof |
| CN114656498A (en) * | 2022-03-29 | 2022-06-24 | 常熟理工学院 | Organic silicon modified sarcosine and preparation method thereof |
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