CN104130415A - Organosilicon quaternary ammonium salt containing alkyl group and glycosylamide group, and preparation method thereof - Google Patents
Organosilicon quaternary ammonium salt containing alkyl group and glycosylamide group, and preparation method thereof Download PDFInfo
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- CN104130415A CN104130415A CN201410336249.XA CN201410336249A CN104130415A CN 104130415 A CN104130415 A CN 104130415A CN 201410336249 A CN201410336249 A CN 201410336249A CN 104130415 A CN104130415 A CN 104130415A
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Abstract
The invention discloses an organosilicon quaternary ammonium salt containing alkyl group and glycosylamide group, and a preparation method thereof. The invention relates to the technical field of organic compound synthesis. The substance is a compound obtained by a bonding reaction with silicon and nitrogen, oxygen or carbon formed in molecules. The preparation method comprises the following steps: dimethyl aminoalkyl glycosylamide is produced by using N,N-dimethyl alkyl diamine and sugar acid or sugar acid lactone in a low-carbon alcohol solvent; the dimethyl aminoalkyl glycosylamide is subjected to a reaction with chloropropyl silane in a polar solvent under the catalysis of an inorganic iodide; after extraction, glycosylamide-modified silane quaternary ammonium salt is obtained; and the glycosylamide-modified silane quaternary ammonium salt is subjected to a reaction with hexamethyldisiloxane, cyclosiloxane and alkylsilane under the effect of an alkaline catalyst, such that the organosilicon quaternary ammonium salt containing alkyl group and glycosylamide group is obtained. The product has a surface tension of 21-23mN/m, and is applied in cosmetic formulas as a cosmetic humectant and emulsifier.
Description
Technical field
The present invention relates in molecule, form siliceous bonding, be with or without the compound that nitrogen, oxygen or bond with carbon reaction obtain, especially relate to a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group and preparation method thereof.
Background technology
Organic silicon surfactant is except having the character of conventional surfactants, also have than the more superiority of conventional surfactants, can be applied to non-aqueous system, there is lower surface tension, good wetting and spreadability, low temperature does not precipitate, extremely low physiology toxicity, high and low temperature resistance etc.
Wagner R. (Applied Organometallic Chemistry, 1996,10,437) reported a kind of method of preparing sugared amoyl modified polysiloxane, by quadrol, epoxy-modified polysiloxane and glucose are coupled together, obtain sugared amoyl modified polysiloxane.
Von Braunm ü hl V (Polymer, 1998,39,1617) reported a kind of method of preparing glucosyacylamino modified polyorganosiloxane, the addition reaction of silicon with hydrogen by hydrogen containing siloxane and allyl group glucamide obtains glucosyacylamino modified polyorganosiloxane.
Han Fu (Journal of Surfactants and Detergents, 2004,7,175) reported a kind of method of preparing glucosyacylamino modification trisiloxanes Gemini surface active agent, by amino trisiloxanes, react with Gluconolactone, generate glucosyacylamino trisiloxanes, then connect and obtain glucosyacylamino modification trisiloxanes Gemini surface active agent with dibasic alcohol glycidyl ether.
Organic silicon surfactant silicone emulsion/the aqueous systems of these sugary amide group is relatively good, but poor to alkane/aqueous systems.And all not containing quaternary ammonium group, the adsorptive power in liquid-solid interface is poor.
Summary of the invention
The object of the invention is the high biological degradability of the low surface tension of organic silicon surfactant and sugar surfactants to combine, and in molecule, introduce chain alkyl and quaternary ammonium group, provide that a kind of surface tension is low, biological degradability good, in liquid-solid interface high adsorption capacity, to alkane and silicone oil emulsification ability all preferably containing the preparation method of the organosilicon quaternary ammonium salt tensio-active agent of alkyl and sugared amide group.
The molecular structural formula of the organosilicon quaternary ammonium salt tensio-active agent containing alkyl and sugared amide group of the present invention is as follows:
Wherein, R
1alkyl for carbon number 4～20.
R
2for
R
3for
R
4for
-H or
X, y, the integer that z is 1～20; N is 2～6 integer.
The preparation method of the organosilicon quaternary ammonium salt containing alkyl and sugared amide group of the present invention comprises the following steps:
1.N, N-dimethyl alkyl diamine and saccharic acid or saccharic acid lactone, make solvent in low-carbon alcohol, and temperature of reaction is 60～150 ℃, preferably 60～100 ℃ of reactions; N wherein, mole proportioning of N-dimethyl alkyl diamine and saccharic acid or saccharic acid lactone is 1～2: 1, preferably 1: 1; After having reacted, steaming desolventizes, and obtains dimethylamino alkyl sugar acid amides;
2. chloropropyl silane, dimethylamino alkyl sugar acid amides and inorganic iodide catalyst, in polar solvent, temperature of reaction is 60～120 ℃, preferably in the situation of 70～100 ℃, reacts; Wherein mole proportioning of chloropropyl silane and dimethylamino alkyl sugar acid amides is (1～10): 1, preferably (2～8): 1, the mole dosage of inorganic iodide catalyst is 0.1%～10% of chloropropyl silane and dimethylamino alkyl sugar acid amides mole sum; After having reacted, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification;
3. by silane quaternary ammonium salt and the basic catalyst of hexamethyldisiloxane, cyclosiloxane, alkyl silane, sugared acid amides modification, in temperature of reaction, be 50～200 ℃, preferably in the situation of 50～150 ℃, react; Wherein mole proportioning of the silane quaternary ammonium salt of hexamethyldisiloxane, cyclosiloxane, alkyl silane and sugared acid amides modification is 1: (1～6): (0.4～2): (0.6～2), preferably 1: (2～4): (0.4～1): (0.6～1), the mole dosage of basic catalyst be hexamethyldisiloxane, cyclosiloxane, alkyl silane and sugared acid amides modification silane quaternary ammonium salt mole sum 0.1%～10%; After having reacted, make basic catalyst inactivation, underpressure distillation, removes low-boiling-point substance, obtains the organosilicon quaternary ammonium salt containing alkyl and sugared amide group.
N as above, N-dimethyl alkyl diamine can comprise: N, N-dimethyl-ethylenediamine, N, N-dimethylated propyl diethylenetriamine, N, N-diamine dimethyl butyrate, N, N-dimethyl-penten diamines, N, N-dimethyl hexanediamine etc.
Saccharic acid as above or saccharic acid lactone can comprise: glucose saccharic acid or glucose saccharic acid lactone, lactobionic acid or lactobionic acid lactone, mannonic acid or mannonic acid lactone etc.
Low-carbon alcohol as above can comprise: methyl alcohol, ethanol, n-propyl alcohol, Virahol etc.
Chloropropyl silane as above can comprise: chloropropyl dimethoxy-methyl silane, chloropropyl diethoxymethyl silane etc.
Inorganic iodide catalyst as above can comprise: sodium iodide, potassiumiodide, magnesium iodide etc.
Polar solvent as above can comprise: phenylcarbinol, oil of mirbane, chlorobenzene, dimethylbenzene, propyl carbinol, Virahol, propylene glycol, methyl-sulphoxide, tetrahydrofuran (THF), DMF etc.
Cyclosiloxane as above comprises: hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane and composition thereof etc.
Alkyl silane as above can comprise: butyl dimethoxy-methyl silane, butyl diethoxymethyl silane, hexyl dimethoxy-methyl silane, hexyl diethoxymethyl silane, octyl group dimethoxy-methyl silane, octyl group diethoxymethyl silane, decyl dimethoxy-methyl silane, decyl diethoxymethyl silane, lauryl dimethoxy-methyl silane, lauryl diethoxymethyl silane, tetradecyl dimethoxy-methyl silane, tetradecyl diethoxymethyl silane, hexadecyl dimethoxy-methyl silane, hexadecyl diethoxymethyl silane etc.
Basic catalyst as above can comprise: alkali metal hydroxide is as sodium hydroxide, potassium hydroxide etc., and silicon alkoxide is as sodium silanolate, silanol potassium etc., and quaternary ammonium hydroxide is if the ， quaternary phosphonium hydroxides such as Tetramethylammonium hydroxide are as Si butyl phosphonium hydroxides etc.
The basic catalyst inactivation that makes as above is when basic catalyst is alkali metal hydroxide, silicon alkoxide, adds sour catalyst neutralisation, makes it inactivation; When basic catalyst is quaternary ammonium hydroxide, quaternary phosphonium hydroxide, thermal degradation, makes it inactivation.
The organosilicon quaternary ammonium salt tensio-active agent containing alkyl and sugared amide group that the present invention is prepared, its advantage is that the high biological degradability of the low surface tension of organic silicon surfactant and sugar surfactants is combined, and in molecule, introduce chain alkyl and quaternary ammonium salt, adsorptive power in liquid-solid interface is stronger, all better to the emulsifying capacity of alkane and silicone oil.Can be used as cosmetic humectant, emulsifying agent for cosmetic formulations.Its using method and other cosmetic material are similar.
Embodiment
Below in conjunction with embodiment, the present invention is made an explanation.
Embodiment 1
In reactor 1, add N, N-dimethyl-ethylenediamine 0.88kg, Gluconolactone 1.78kg, makes solvent with methyl alcohol, is heated to 60 ℃, reacts 8 hours, steams and desolventizes methyl alcohol, obtains N, N-dimethyl ethyl glucamide.In reactor 2, add chloropropyl dimethoxy-methyl silane 1.83kg, N, N-dimethyl ethyl glucamide 2.66kg, potassiumiodide 0.003kg, makes solvent with Virahol, is heated to 60 ℃, react 20 hours, steaming desolventizes, and extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, hexamethyl cyclotrisiloxane 8.88kg, hexadecyl dimethoxy-methyl silane 1.32kg, the silane quaternary ammonium salt 2.69kg of sugared acid amides modification, Tetramethylammonium hydroxide 21.72g, heating for dissolving, temperature is controlled at 100 ℃, reacts after 4 hours, intensification is heated to 130 ℃, make catalyst deactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 21.7mN/m.
Embodiment 2
In reactor 1, add N, N-dimethylated propyl diethylenetriamine 1.02kg, gluconic acid 1.96kg, makes solvent with ethanol, is heated to 70 ℃, reacts 8 hours, steams and desolventizes ethanol, obtains N, N-dimethyl propyl glucamide.In reactor 2, add chloropropyl dimethoxy-methyl silane 3.66kg, N, N-dimethyl propyl glucamide 2.80kg, sodium iodide 0.09kg, with Virahol, make solvent, be heated to 70 ℃, react 24 hours, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, octamethylcyclotetrasiloxane 8.88kg, octyl dimethoxy-methyl silane 1.09kg, the silane quaternary ammonium salt 4.63kg of sugared acid amides modification, potassium hydroxide 36.40g, heating for dissolving, temperature is controlled at 120 ℃, reacts after 5 hours, add acetic acid catalyst neutralisation, make it inactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 22.0mN/m.
Embodiment 3
In reactor 1, add N, N-diamine dimethyl butyrate 1.16kg, mannonic acid lactone 1.78kg, makes solvent with methyl alcohol, is heated to 80 ℃, reacts 10 hours, steams and desolventizes methyl alcohol, obtains N, N-dimethylbutyl seminose acid amides.In reactor 2, add chloropropyl dimethoxy-methyl silane 5.49kg, N, N-dimethylbutyl seminose acid amides 2.94kg, potassiumiodide 0.26kg, with propyl carbinol, make solvent, be heated to 80 ℃, react 24 hours, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, hexamethyl cyclotrisiloxane 4.44kg, lauryl dimethoxy-methyl silane 1.37kg, the silane quaternary ammonium salt 9.54kg of sugared acid amides modification, Si butyl phosphonium hydroxides 1.52g, heating for dissolving, temperature is controlled at 80 ℃, reacts after 4 hours, intensification is heated to 110 ℃, make catalyst deactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 22.4mN/m.
Embodiment 4
In reactor 1, add N, N-dimethyl hexanediamine 1.44kg, mannonic acid 1.96kg, makes solvent with ethanol, is heated to 90 ℃, reacts 10 hours, steams and desolventizes ethanol, obtains N, N-dimethyl hexyl seminose acid amides.In reactor 2, add chloropropyl dimethoxy-methyl silane 7.32kg, N, N-dimethyl hexyl seminose acid amides 3.22kg, sodium iodide 0.37kg, with propyl carbinol, make solvent, be heated to 90 ℃, react 24 hours, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, octamethylcyclotetrasiloxane 5.92kg, lauryl diethoxymethyl silane 1.51kg, the silane quaternary ammonium salt 3.03kg of sugared acid amides modification, silanol potassium 2.64g, heating for dissolving, temperature is controlled at 90 ℃, reacts after 5 hours, add acetic acid catalyst neutralisation, make it inactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 21.3mN/m.
Embodiment 5
In reactor 1, add N, N-dimethyl-ethylenediamine 0.88kg, lactobionic acid lactone 3.40kg, makes solvent with methyl alcohol, is heated to 100 ℃, reacts 8 hours, steams and desolventizes methyl alcohol, obtains N, N-dimethyl ethyl lactose amide.In reactor 2, add chloropropyl diethoxymethyl silane 12.66kg, N, N-dimethyl ethyl lactose amide 4.28kg, potassiumiodide 0.70kg, with propylene glycol, make solvent, be heated to 90 ℃, react 20 hours, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, hexamethyl cyclotrisiloxane 6.66kg, decyl dimethoxy-methyl silane 1.23kg, the silane quaternary ammonium salt 6.39kg of sugared acid amides modification, Tetramethylammonium hydroxide 14.93g, heating for dissolving, temperature is controlled at 60 ℃, reacts after 5 hours, intensification is heated to 135 ℃, make catalyst deactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 22.6mN/m.
Embodiment 6
In reactor 1, add N, N-dimethylated propyl diethylenetriamine 1.02kg, lactobionic acid 3.58kg, makes solvent with ethanol, is heated to 120 ℃, reacts 8 hours, steams and desolventizes ethanol, obtains N, N-dimethyl propyl lactose amide.In reactor 2, add chloropropyl diethoxymethyl silane 14.77kg, N, N-dimethyl propyl lactose amide 4.42kg, sodium iodide 0.84kg, with propylene glycol, make solvent, be heated to 100 ℃, react 20 hours, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, octamethylcyclotetrasiloxane 8.88kg, octyl dimethoxy-methyl silane 1.09kg, the silane quaternary ammonium salt 6.53kg of sugared acid amides modification, potassium hydroxide 15.40g, heating for dissolving, temperature is controlled at 80 ℃, reacts after 4 hours, add acetic acid catalyst neutralisation, make it inactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 22.7mN/m.
Embodiment 7
In reactor 1, add N, N-diamine dimethyl butyrate 1.16kg, lactobionic acid lactone 3.40kg, makes solvent with methyl alcohol, is heated to 140 ℃, reacts 9 hours, steams and desolventizes methyl alcohol, obtains N, N-dimethylbutyl lactose amide.In reactor 2, add chloropropyl diethoxymethyl silane 16.88kg, N, N-dimethylbutyl lactose amide 4.56kg, potassiumiodide 1.20kg, with phenylcarbinol, make solvent, be heated to 110 ℃, react 20 hours, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, hexamethyl cyclotrisiloxane 4.44kg, lauryl dimethoxy-methyl silane 1.37kg, the silane quaternary ammonium salt 13.34kg of sugared acid amides modification, Tetramethylammonium hydroxide 7.96g, heating for dissolving, temperature is controlled at 120 ℃, reacts after 4 hours, intensification is heated to 130 ℃, make catalyst deactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 22.6mN/m.
Embodiment 8
In reactor 1, add N, N-dimethyl hexanediamine 1.44kg, lactobionic acid 3.58kg, makes solvent with ethanol, is heated to 150 ℃, reacts 9 hours, steams and desolventizes ethanol, obtains N, N-dimethyl hexyl lactose amide.In reactor 2, add chloropropyl diethoxymethyl silane 21.10kg, N, N-dimethyl hexyl lactose amide 4.84kg, sodium iodide 1.81kg, with phenylcarbinol, make solvent, be heated to 120 ℃, react 20 hours, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification.In reactor 3, add hexamethyldisiloxane 1.62kg, octamethylcyclotetrasiloxane 5.92kg, decyl dimethoxy-methyl silane 1.23kg, the silane quaternary ammonium salt 13.90kg of sugared acid amides modification, potassium hydroxide 3.08g, heating for dissolving, temperature is controlled at 100 ℃, reacts after 5 hours, add acetic acid catalyst neutralisation, make it inactivation, remove low-boiling-point substance under reduced pressure, obtain product.Recording its lowest surface tension is 21.8mN/m.
Claims (13)
1. containing an organosilicon quaternary ammonium salt for alkyl and sugared amide group, it is characterized in that containing the molecular structural formula of the organosilicon quaternary ammonium salt of alkyl and sugared amide group as follows:
Wherein, R
1alkyl for carbon number 4～20.
R
2for
R
3for
R
4for
-H or
X, y, the integer that z is 1～20; N is 2～6 integer.
2. contain a preparation method for the organosilicon quaternary ammonium salt of alkyl and sugared amide group, it is characterized in that comprising the steps:
(1) N, N-dimethyl alkyl diamine and saccharic acid or saccharic acid lactone, make solvent in low-carbon alcohol, and temperature of reaction is 60～150 ℃ of reactions; N wherein, mole proportioning of N-dimethyl alkyl diamine and saccharic acid or saccharic acid lactone is 1～2: 1; After having reacted, steaming desolventizes, and obtains dimethylamino alkyl sugar acid amides;
(2) chloropropyl silane, dimethylamino alkyl sugar acid amides and inorganic iodide catalyst, in polar solvent, temperature of reaction is to react in the situation of 60～120 ℃; Wherein mole proportioning of chloropropyl silane and dimethylamino alkyl sugar acid amides is (1～10): 1, and the mole dosage of inorganic iodide catalyst is 0.1%～10% of chloropropyl silane and dimethylamino alkyl sugar acid amides mole sum; After having reacted, remove solvent and excess reactant under reduced pressure, extraction obtains the silane quaternary ammonium salt of sugared acid amides modification;
(3) by silane quaternary ammonium salt and the basic catalyst of hexamethyldisiloxane, cyclosiloxane, alkyl silane, sugared acid amides modification, in the situation that being 50～200 ℃, temperature of reaction reacts; Wherein mole proportioning of the silane quaternary ammonium salt of hexamethyldisiloxane, cyclosiloxane, alkyl silane and sugared acid amides modification is 1: (1～6): (0.4～2): (0.6～2), the mole dosage of basic catalyst be hexamethyldisiloxane, cyclosiloxane, alkyl silane and sugared acid amides modification silane quaternary ammonium salt mole sum 0.1%～10%; After having reacted, make basic catalyst inactivation, underpressure distillation, removes low-boiling-point substance, obtains the organosilicon quaternary ammonium salt containing alkyl and sugared amide group.
3. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, it is characterized in that described N, N-dimethyl alkyl diamine is N, N-dimethyl-ethylenediamine, N, N-dimethylated propyl diethylenetriamine, N, N-diamine dimethyl butyrate, N, N-dimethyl-penten diamines, N, N-dimethyl hexanediamine.
4. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, is characterized in that described saccharic acid or saccharic acid lactone are glucose saccharic acid or glucose saccharic acid lactone, lactobionic acid or lactobionic acid lactone, mannonic acid or mannonic acid lactone.
5. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, is characterized in that described low-carbon alcohol is methyl alcohol, ethanol, n-propyl alcohol, Virahol.
6. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, is characterized in that described chloropropyl silane is chloropropyl dimethoxy-methyl silane, chloropropyl diethoxymethyl silane.
7. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, is characterized in that described inorganic iodide catalyst is sodium iodide, potassiumiodide, magnesium iodide.
8. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, it is characterized in that described polar solvent is phenylcarbinol, oil of mirbane, chlorobenzene, dimethylbenzene, propyl carbinol, Virahol, propylene glycol, methyl-sulphoxide, tetrahydrofuran (THF), DMF.
9. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, is characterized in that described cyclosiloxane is hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane and composition thereof.
10. the preparation method of a kind of organosilicon quaternary ammonium salt containing alkyl and sugared amide group as claimed in claim 2, it is characterized in that described alkyl silane is butyl dimethoxy-methyl silane, butyl diethoxymethyl silane, hexyl dimethoxy-methyl silane, hexyl diethoxymethyl silane, octyl group dimethoxy-methyl silane, octyl group diethoxymethyl silane, decyl dimethoxy-methyl silane, decyl diethoxymethyl silane, lauryl dimethoxy-methyl silane, lauryl diethoxymethyl silane, tetradecyl dimethoxy-methyl silane, tetradecyl diethoxymethyl silane, hexadecyl dimethoxy-methyl silane, hexadecyl diethoxymethyl silane.
The preparation method of 11. a kind of organosilicon quaternary ammonium salts containing alkyl and sugared amide group as claimed in claim 2, is characterized in that described basic catalyst is alkali metal hydroxide, silicon alkoxide, quaternary ammonium hydroxide, quaternary phosphonium hydroxide.
The preparation method of 12. a kind of organosilicon quaternary ammonium salts containing alkyl and sugared amide group as claimed in claim 11, it is characterized in that described alkali metal hydroxide is sodium hydroxide, potassium hydroxide, silicon alkoxide is sodium silanolate, silanol potassium, quaternary ammonium hydroxide is that Tetramethylammonium hydroxide ， quaternary phosphonium hydroxide is Si butyl phosphonium hydroxides.
The preparation method of 13. a kind of organosilicon quaternary ammonium salts containing alkyl and sugared amide group as claimed in claim 2, it is characterized in that the described basic catalyst inactivation that makes is when basic catalyst is alkali metal hydroxide, silicon alkoxide, add sour catalyst neutralisation, make it inactivation; When basic catalyst is quaternary ammonium hydroxide, quaternary phosphonium hydroxide, thermal degradation, makes it inactivation.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108409968A (en) * | 2018-03-29 | 2018-08-17 | 中国日用化学研究院有限公司 | A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant |
| CN111808289A (en) * | 2020-06-22 | 2020-10-23 | 广东标美硅氟新材料有限公司 | Sugar-modified silicone oil and application thereof |
| CN112409598A (en) * | 2020-11-19 | 2021-02-26 | 广东工业大学 | Bola type organosilicon quaternary ammonium salt, preparation method and application thereof |
| US11116220B2 (en) | 2017-12-22 | 2021-09-14 | Ecolab Usa Inc. | Antimicrobial compositions with enhanced efficacy |
-
2014
- 2014-07-15 CN CN201410336249.XA patent/CN104130415A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11116220B2 (en) | 2017-12-22 | 2021-09-14 | Ecolab Usa Inc. | Antimicrobial compositions with enhanced efficacy |
| US11930819B2 (en) | 2017-12-22 | 2024-03-19 | Ecolab Usa Inc. | Antimicrobial compositions with enhanced efficacy |
| CN108409968A (en) * | 2018-03-29 | 2018-08-17 | 中国日用化学研究院有限公司 | A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant |
| CN111808289A (en) * | 2020-06-22 | 2020-10-23 | 广东标美硅氟新材料有限公司 | Sugar-modified silicone oil and application thereof |
| CN111808289B (en) * | 2020-06-22 | 2023-05-30 | 广东标美硅氟新材料有限公司 | Sugar modified silicone oil and application thereof |
| CN112409598A (en) * | 2020-11-19 | 2021-02-26 | 广东工业大学 | Bola type organosilicon quaternary ammonium salt, preparation method and application thereof |
| CN112409598B (en) * | 2020-11-19 | 2021-06-01 | 广东工业大学 | Bola type organosilicon quaternary ammonium salt, preparation method and application thereof |
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