CN108409968A - A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant - Google Patents
A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant Download PDFInfo
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- CN108409968A CN108409968A CN201810271391.9A CN201810271391A CN108409968A CN 108409968 A CN108409968 A CN 108409968A CN 201810271391 A CN201810271391 A CN 201810271391A CN 108409968 A CN108409968 A CN 108409968A
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- glucoheptose
- sugar
- organosilicon
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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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/008—Polymeric surface-active agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/82—Compounds containing silicon
Abstract
A kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant is using low-boiling point alcohol as solvent, and glucoheptose sugar lactone, amino silane are raw material；14 h are reacted under the conditions of 50 150 DEG C；Low boiling point solvent is steamed after reaction, obtains glucoheptose sugar amide silane；With glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, 25 h of reaction make catalyst inactivation after reaction under the conditions of 70 150 DEG C, obtain high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant.The present invention has the advantages that preparation is simple, low energy consumption, grafting rate agent is high, good water solubility.
Description
Technical field
The invention belongs to synthesis of surfactant field, a kind of washing is related generally to, high grafting rate combed used for cosmetic has
The preparation method of machine silicon glucoheptose sugar acidamide surfactant.
Technical background
The existing preparation method hydrosilation method and bulk polymerization-Graft Method for preparing organosilicon sugar amide.
It is relatively more for the relevant report of hydrosilation method, as Wagner R report a kind of system of organosilicon glucamide
Preparation Method is that epoxy-modified polysiloxane is prepared using containing hydrogen silicone oil and allyl glycidyl ether as raw material, then and mistake
The reacting ethylenediamine of amount obtains amino modified polysiloxane, and organosilicon glucamide is finally obtained by the reaction with sugar lactone, in addition, also
Some are then to carry out hydrosilation method by containing hydrogen silicone oil and allyl ammonia to obtain amido silicon oil, subsequent amino silane in sugar
Organosilicon glucamide is obtained by the reaction in ester.However, in these synthetic methods, there are hydrosilation method, reaction used catalyst more
It is expensive for chloroplatinic acid, and the reaction time is longer.
And CN101942097B reports a kind of preparation method of organosilicon glucamide, first passes through cyclosiloxane, amino
Silane, hexamethyl siloxane are that raw material carries out bulk polymerization, then carry out glycosyl and be modified to obtain organosilicon glucamide, the method without
It is malicious, at low cost, but since glycosyl grafting rate is relatively low, the water solubility of product is poor, influences its application range.
Invention content
The purpose of the present invention is overcome existing technological deficiency with it is insufficient, provide and a kind of prepare that simple, low energy consumption, grafting rate
The preparation method of high, good water solubility high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant.
The preparation path of the present invention is as follows：
(1) glucoheptose sugar lactones is reacted with amino silane, prepares glucoheptose sugar amide silane：
Wherein, R1For CH3Or C2H5；N is the integer of 1-6.
(2) it with glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, prepares
High grafting rate combed organosilicon glucoheptose sugar acidamide surfactant：
Wherein, X is the integer of 5-10；P is the integer of 4-60；M is the integer of 10-200.
A kind of preparation method of high grafting rate organosilicon glucoheptose sugar acidamide surfactant of the present invention, including walk as follows
Suddenly：
(1) using low-boiling point alcohol as solvent, glucoheptose sugar lactone, amino silane are raw material；It is reacted under the conditions of 50-150 DEG C
1-4h；Low boiling point solvent is steamed after reaction, obtains glucoheptose sugar amide silane；
(2) with glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, in
2-5h is reacted under the conditions of 70-150 DEG C, after reaction, makes catalyst inactivation, obtains high grafting rate combed organosilicon glucoheptose sugar
Acidamide surfactant.
Glucoheptose sugar lactones is as described above：
Amino silane is as described above：
Wherein R1For CH3Or C2H5, n is the integer of 1-6.
Cyclosiloxane is as described above：
Wherein, X is the integer of 5-10.
As described above, low boiling point solvent used is one kind of the low boiling point solvents such as methanol, ethyl alcohol, isopropanol in step (1)
Or it is several.Solvent usage amount is 5-10 times of glucoheptose sugar lactone quality.
As described above, the molar ratio of glucoheptose sugar lactone and amino silane is 1 in step (1):6-1:1, preferably 1:4-1:
1；Preferred 60-100 DEG C of reaction temperature；Reaction time preferred 1.5-3.5h.
As described above, the molar ratio of glucoheptose sugar amide silane in step (2), cyclosiloxane, hexamethyldisiloxane is
1-40:0.5-20:1, preferably 2-30:1-10:1；Preferred 80-120 DEG C of reaction temperature；Reaction time preferred 2-4h.
As described above, step (2) catalyst be alkali metal hydroxide such as sodium hydroxide etc., silicon alkoxide such as sodium silanolate etc.,
Quaternary ammonium base such as tetramethylammonium hydroxide etc., silanol quaternary ammonium salt such as tetramethyl silanol ammonium etc..Catalyst amount is cyclosiloxane quality
0.01%-2%, preferably 0.1%-2%.
As described above, there are mainly two types of modes for step (2) catalyst inactivation：When catalyst is alkali metal hydroxide, silicon
When alkoxide, acid, which is added, makes it lose catalytic activity, and is removed through filtering；When catalyst is quaternary ammonium base, silanol quaternary ammonium salt, heating
It is set to decompose inactivation.
The present invention compared with having technology the same as having the following advantages that：
1, high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant prepared by the present invention, grafting rate are up to
95%-98% has larger dissolubility (solubility is 1-30g/100g water) in aqueous solution, and the surface tension of aqueous solution is
21.0-29.0mN·m-1；Critical micelle concentration is 25-1000mgL-1.It is easy to prepare in household chemicals, in daily use chemicals etc.
Field has potential application.
2, grafting time used in preparation process of the present invention is shorter, more energy saving, and grafting rate higher is more advantageous to industrialization.
Description of the drawings
Fig. 1 is the infrared spectrogram of organosilicon glucoheptose sugar acidamide surfactant.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of organosilicon glucoheptose sugar acidamide surfactant.
Specific implementation mode
It enumerates specific example below to illustrate patent of the present invention, but the present invention is not limited in following embodiment.
Embodiment 1：
17.80g glucoheptose sugar lactones are added in flask, 100mL is added in 19.10g aminopropyl diethoxymethylsilanes
Methanol makees solvent, at 80 DEG C, reacts 2h, distillation removal methanol obtains glucamide diethoxymethylsilane.Add in flask
Enter 19.10g glucoheptose sugar amides diethoxymethylsilane, decamethylcyclopentaandoxane 20.00g, hexamethyl siloxane
3.70g, addition 0.08g tetramethylammonium hydroxide are catalyst, react 4h at 90 DEG C；After reaction, being heated to 134 DEG C makes
Catalyst inactivation, you can obtain organosilicon glucoheptose sugar acidamide surfactant.Primaquine value, meter are measured by non-hyperbolic curve
It is 95% to calculate grafting rate；The surface tension of products therefrom is 24.3mNm-1, critical micelle concentration 52mgL-1, solubility
For 5g/100g water.
Embodiment 2：
15.00g glucoheptose sugar lactones are added in flask, 140mL is added in 19.10g aminopropyl dimethoxy methyl-monosilanes
Ethyl alcohol makees solvent, at 90 DEG C, reacts 3h, distillation removal ethyl alcohol obtains glucoheptose sugar amide dimethoxymethylsilane.In flask
Middle addition 32.10g glucoheptose sugar amides dimethoxymethylsilane, ten pregnancy basic rings, eight siloxanes 100.00g, hexamethyl silica
Alkane 3.20g, it is catalyst 8.10g that the trimethyl silicane potassium alcoholate that mass fraction is 1.5%, which is added, reacts 3h at 85 DEG C；Reaction knot
Shu Hou, being heated to 134 DEG C makes catalyst inactivation, you can obtains organosilicon glucoheptose sugar acidamide surfactant.Pass through non-water power
Position titration determination primaquine value, it is 98% to calculate grafting rate；The surface tension of products therefrom is 22.4mNm-1, critical micelle concentration
For 390mgL-1, solubility is 9g/100g water.
Embodiment 3：
20.7g glucoheptose sugar lactones are added in flask, 30.6g aminoethylaminopropyl dimethoxymethylsilanes are added
200mL isopropanols make solvent, at 95 DEG C, react 1.5h, distillation removal isopropanol obtains glucoheptose sugar amide dimethoxy-methyl
Silane.It is added 92.10g glucoheptose sugar amides dimethoxymethylsilanes, ten prestox rings nine siloxanes 180g in flask, six
Methylsiloxane 1.60g, addition 1.8g potassium hydroxide are catalyst, react 4h at 110 DEG C；After reaction, acetic acid is added to make
Catalyst inactivation, filtering can be obtained organosilicon glucoheptose sugar acidamide surfactant.Primaquine is measured by non-hyperbolic curve
Value, it is 97.5% to calculate grafting rate；The surface tension of products therefrom is 26.4mNm-1, critical micelle concentration 740mgL-1, solubility is 15g/100g water.
Embodiment 4：
9.58g glucoheptose sugar lactones are added in flask, 90mL first is added in 26.40g aminopropyl dimethoxy methyl-monosilanes
Alcohol makees solvent, at 90 DEG C, reacts 3.5h, distillation removal methanol obtains glucoheptose sugar amide dimethoxymethylsilane.In flask
Middle addition 24.10g glucoheptose sugar amides dimethoxymethylsilane, ten diformazan basic rings, six siloxanes 89.10g, hexamethyl silica
Alkane 3.20g, addition 0.40g sodium hydroxides are catalyst, react 2.5h at 90 DEG C；After reaction, acetic acid is added to make catalyst
Inactivation, filtering can be obtained organosilicon glucoheptose sugar acidamide surfactant.Primaquine value is measured by non-hyperbolic curve, is calculated
Grafting rate is 98%；The surface tension of products therefrom is 24.3mNm-1, critical micelle concentration 980mgL-1, solubility is
26g/100g water.
Embodiment 5：
12.30g glucoheptose sugar lactones are added in flask, 95mL is added in 32.10g aminopropyl dimethoxy methyl-monosilanes
Methanol makees solvent, at 95 DEG C, reacts 3h, distillation removal methanol obtains glucoheptose sugar amide dimethoxymethylsilane.In flask
Middle addition 53.34g glucoheptose sugar amides dimethoxymethylsilane, ten diformazan basic rings, six siloxanes 79.10g, hexamethyl silica
Alkane 3.20g, addition 0.35g sodium hydroxides are catalyst, react 3h at 85 DEG C；After reaction, add acetic acid that catalyst is made to lose
Living, filtering can be obtained organosilicon glucoheptose sugar acidamide surfactant.Primaquine value is measured by non-hyperbolic curve, calculating connects
Branch rate is 98.5%；The surface tension of products therefrom is 26.4mNm-1, critical micelle concentration 894mgL-1, solubility is
32g/100g water.
Claims (17)
1. a kind of preparation method of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant, it is characterised in that including such as
Lower step：
(1) using low-boiling point alcohol as solvent, glucoheptose sugar lactone, amino silane are raw material；1-4h is reacted under the conditions of 50-150 DEG C；
Low boiling point solvent is steamed after reaction, obtains glucoheptose sugar amide silane；
(2) with glucoheptose sugar amide silane, cyclosiloxane, hexamethyldisiloxane raw material, under the action of catalyst, in 70-150
2-5h is reacted under the conditions of DEG C, after reaction, makes catalyst inactivation, obtains high grafting rate combed organosilicon glucoheptose sugar amide table
Face activating agent.
2. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that the glucoheptose sugar lactones is：
3. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that amino silane is：
Wherein R1For CH3Or C2H5, n is the integer of 1-6.
4. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that cyclosiloxane is：
Wherein, X is the integer of 5-10.
5. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that low boiling point solvent used is one or more of methanol, ethyl alcohol, isopropanol, solvent in the step (1)
Usage amount is 5-10 times of glucoheptose sugar lactone quality.
6. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that the molar ratio of glucoheptose sugar lactone and amino silane is 1 in the step (1):6-1:1.
7. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 6
Method, it is characterised in that the molar ratio of glucoheptose sugar lactone and amino silane is 1 in the step (1):4-1:1.
8. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that reaction temperature is 60-100 DEG C in the step (1)；Reaction time is 1.5-3.5h.
9. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that glucoheptose sugar amide silane in the step (2), cyclosiloxane, hexamethyldisiloxane molar ratio be
1-40:0.5-20:1。
10. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 9
Method, it is characterised in that glucoheptose sugar amide silane in the step (2), cyclosiloxane, hexamethyldisiloxane molar ratio be
2-30:1-10:1。
11. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that reaction temperature is 80-120 DEG C in the step (2)；Reaction time is 2-4h.
12. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that step (2) catalyst is alkali metal hydroxide, silicon alkoxide, quaternary ammonium base or silanol quaternary ammonium salt.
13. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 12
Method, it is characterised in that alkali metal hydroxide is sodium hydroxide, and silicon alkoxide is sodium silanolate, and quaternary ammonium base is tetramethylammonium hydroxide,
Silanol quaternary ammonium salt is tetramethyl silanol ammonium.
14. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that step (2) catalyst amount is the 0.01%-2% of cyclosiloxane quality.
15. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as claimed in claim 14
Method, it is characterised in that step (2) catalyst amount is the 0.1%-2% of cyclosiloxane quality.
16. a kind of preparation side of high grafting rate combed organosilicon glucoheptose sugar acidamide surfactant as described in claim 1
Method, it is characterised in that there are two types of modes for step (2) catalyst inactivation：When catalyst is alkali metal hydroxide, silicon alkoxide
When, acid, which is added, makes it lose catalytic activity, and is removed through filtering；When catalyst is quaternary ammonium base, silanol quaternary ammonium salt, heating makes it
Decompose inactivation.
17. the high grafting rate combed organosilicon glucoheptose sugar amide surface as prepared by any one of claim 1-16 the methods is lived
Property agent, it is characterised in that
Wherein；P is the integer of 4-60；M is the integer of 10-200.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109106608A (en) * | 2018-09-18 | 2019-01-01 | 中国日用化学研究院有限公司 | A kind of cleaning skin solid particle and the facial cleanser and preparation method thereof for preventing skin deposits solid particle |
| CN110437272A (en) * | 2019-08-05 | 2019-11-12 | 中国日用化学研究院有限公司 | A kind of preparation method of ABA type organosilicon glucoheptonic acid acidamide surfactant |
| CN111449993A (en) * | 2020-04-27 | 2020-07-28 | 中国日用化学研究院有限公司 | Foam type low-carbon alcohol system hand disinfectant and preparation method thereof |
| CN113024816A (en) * | 2021-03-30 | 2021-06-25 | 中国日用化学研究院有限公司 | Comb-type aminosiloxane-allyl polydimethylsiloxane co-modified organic silicon and preparation method thereof |
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| CN110437272A (en) * | 2019-08-05 | 2019-11-12 | 中国日用化学研究院有限公司 | A kind of preparation method of ABA type organosilicon glucoheptonic acid acidamide surfactant |
| CN110437272B (en) * | 2019-08-05 | 2022-10-11 | 中国日用化学研究院有限公司 | Preparation method of ABA type organosilicon glucoheptonamide surfactant |
| CN111449993A (en) * | 2020-04-27 | 2020-07-28 | 中国日用化学研究院有限公司 | Foam type low-carbon alcohol system hand disinfectant and preparation method thereof |
| CN113024816A (en) * | 2021-03-30 | 2021-06-25 | 中国日用化学研究院有限公司 | Comb-type aminosiloxane-allyl polydimethylsiloxane co-modified organic silicon and preparation method thereof |
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