CN102513027A - Method for preparing organosilicon surfactant containing glucoside group - Google Patents
Method for preparing organosilicon surfactant containing glucoside group Download PDFInfo
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- CN102513027A CN102513027A CN201110402482XA CN201110402482A CN102513027A CN 102513027 A CN102513027 A CN 102513027A CN 201110402482X A CN201110402482X A CN 201110402482XA CN 201110402482 A CN201110402482 A CN 201110402482A CN 102513027 A CN102513027 A CN 102513027A
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Abstract
The invention relates to a preparation method of an organosilicon surfactant containing a glucoside group, which belongs to the organic compound synthesis technical field. The compound containing silicon and oxygen or carbon formed in molecule is obtained by a bonding reaction. The preparation method is characterized in that allyl alcohol or allyl ether, glucose are prepared to obtain allyl glucoside under the acid catalyst effect, and the allyl glucoside is reacted with hydrogen-containing silicone oil under the chloroplatinic acid catalysis effect to obtain the organosilicon surfactant containing the glucoside group, wherein the surface tension is 20-23mNm, and the application is wide.
Description
Technical field
The present invention relates in molecule, form siliceous bonding, be with or without the compound that the reaction of oxygen or bond with carbon obtains, especially relate to a kind of organosilicon that contains glycosyl and preparation method thereof.
Background technology
Organic silicon surfactant is except that the character with conventional surfactants; Also have than the more superiority of conventional surfactants, can be applied to non-aqueous system, have lower surface tension, good wetting and spreadability, low temperature does not precipitate, extremely low physiology toxicity, high and low temperature resistance etc.Reported a kind of method for preparing polyether-modified trisiloxane surfactant like patent CN101690878A, the addition reaction preparation through allyl polyether and hydrogeneous trisiloxanes gets.
APG is by the hemiacetal hydroxyl of glucose and fatty alcohol hydroxyl, under the catalysis of acid, loses a part water and the product that obtains.Have good surface-active and foaming capacity, dirt-removing power is strong, and good synergistic is arranged, and biodegradation is thorough rapidly, nontoxic, nonirritant.Reported a kind of method for preparing alkyl glucoside surfactant like patent CN101696226A, got through DEXTROSE ANHYDROUS or the glycosylation reaction preparation that contains glucose and the long-chain fatty alcohol of a crystallization water.
The biological degradability of organic silicon modified by polyether surfactant is poorer than corresponding non-silicon class polyethet surfactant, and the surface-active of APG is good not as silicone based surfactant.
Summary of the invention
The objective of the invention is the low surface tension of organic silicon surfactant and the high biological degradability of glucosides class surfactant are combined, the preparation method of the organic silicon surfactant that contains glycosyl that a kind of surface tension is low, biological degradability is good is provided.
The molecular structural formula of the organic silicon surfactant that contains glycosyl of the present invention is following:
Wherein, R '=-CH
3Or R;
R does
X, y is 0～100 integer, is preferably 0～20; A is 0～20 integer, is preferably 0～4; B is 1～2.
When y=0, R ' can not be-CH entirely
3
The preparation method who contains the organic silicon surfactant of glycosyl of the present invention may further comprise the steps:
1. by allyl alcohol or allyl ether, glucose and acidic catalyst, be 60～150 ℃, preferably react under 80～120 ℃ the situation in reaction temperature; Wherein the mole proportioning of allyl alcohol or allyl ether and glucose is 2～10: 1, preferably 4～8: 1, and the mole dosage of catalyst is a catalyst: glucose=1～10: 100; Reaction makes the acidic catalyst inactivation after accomplishing, and removes excessive unreacted reactant under reduced pressure, obtains the pi-allyl glucosides;
2. by pi-allyl glucosides, containing hydrogen silicone oil and chloroplatinic acid catalyst, be 60～140 ℃, preferably react under 80～120 ℃ the situation in reaction temperature; Wherein the mole proportioning of si-h bond is 1～2: 1 in pi-allyl glucosides and the containing hydrogen silicone oil, preferably 1～1.1: 1; The mole dosage of catalyst chloroplatinic acid is a chloroplatinic acid: si-h bond=1～10: 100000; After reaction is accomplished, obtain containing the organic silicon surfactant of glycosyl.
Aforesaid acidic catalyst can comprise: sulfuric acid, hydrochloric acid, phosphoric acid, p-methyl benzenesulfonic acid, naphthalene sulfonic acids, alkyl sulfonic acid, sweet-smelling alkyl sulfonic acid etc.
The aforesaid acidic catalyst inactivation that makes is to add the alkali catalyst neutralisation, makes it inactivation.
The organic silicon surfactant that contains glycosyl that the present invention is prepared, its advantage are that the high biological degradability with the low surface tension of organic silicon surfactant and glucosides class surfactant combines, and reaction process is simple, helps industrialization.
The specific embodiment
Below in conjunction with embodiment the present invention is made an explanation.
Embodiment 1
In agitated reactor, add allyl alcohol 2.32kg, glucose 1.80kg, p-methyl benzenesulfonic acid 68.80g, heating for dissolving, temperature are controlled at 100 ℃, under reduced pressure react 6 hours after, hydro-oxidation sodium catalyst neutralisation makes it inactivation.Decompression steams the unreacted allyl alcohol, adds the 5.18kg containing hydrogen silicone oil, is heated to 120 ℃, reacts 8 hours, obtains containing the organic silicon surfactant product of glycosyl, and recording its surface tension is 21.7mN/m.
Embodiment 2
In agitated reactor, add ethylene glycol monoallyl ether 4.08kg, glucose 1.80kg, p-methyl benzenesulfonic acid 103.20g, heating for dissolving, temperature are controlled at 110 ℃, under reduced pressure react 7 hours after, hydro-oxidation sodium catalyst neutralisation makes it inactivation.Decompression steams unreacted ethylene glycol monoallyl ether, adds the 8.14kg containing hydrogen silicone oil, is heated to 120 ℃, reacts 6 hours, obtains containing the organic silicon surfactant product of glycosyl, and recording its surface tension is 22.5mN/m.
Embodiment 3
In agitated reactor, add diethylene glycol mono allyl ether 5.84kg, glucose 1.80kg, p-methyl benzenesulfonic acid 68.80g, heating for dissolving, temperature are controlled at 120 ℃, under reduced pressure react 8 hours after, hydro-oxidation sodium catalyst neutralisation makes it inactivation.Decompression steams unreacted diethylene glycol mono allyl ether, adds the 2.22kg containing hydrogen silicone oil, is heated to 120 ℃, reacts 6 hours, obtains containing the organic silicon surfactant product of glycosyl, and recording its surface tension is 20.2mN/m.
Embodiment 4
In agitated reactor, add allyl alcohol 3.48kg, glucose 1.80kg, p-methyl benzenesulfonic acid 137.60g, heating for dissolving, temperature are controlled at 100 ℃, under reduced pressure react 8 hours after, hydro-oxidation sodium catalyst neutralisation makes it inactivation.Decompression steams unreacted allyl alcohol, adds the 8.14kg containing hydrogen silicone oil, is heated to 120 ℃, reacts 4 hours, obtains containing the organic silicon surfactant product of glycosyl, and recording its surface tension is 21.5mN/m.
Embodiment 5
In agitated reactor, add ethylene glycol monoallyl ether 6.12kg, glucose 1.80kg, p-methyl benzenesulfonic acid 103.20g, heating for dissolving, temperature are controlled at 120 ℃, under reduced pressure react 5 hours after, hydro-oxidation sodium catalyst neutralisation makes it inactivation.Decompression steams unreacted ethylene glycol monoallyl ether, adds the 5.18kg containing hydrogen silicone oil, is heated to 120 ℃, reacts 8 hours, obtains containing the organic silicon surfactant product of glycosyl, and recording its surface tension is 22.8mN/m.
Embodiment 6
In agitated reactor, add diethylene glycol mono allyl ether 8.76kg, glucose 1.80kg, p-methyl benzenesulfonic acid 68.80g, heating for dissolving, temperature are controlled at 120 ℃, under reduced pressure react 6 hours after, hydro-oxidation sodium catalyst neutralisation makes it inactivation.Decompression steams unreacted diethylene glycol mono allyl ether, adds the 2.22kg containing hydrogen silicone oil, is heated to 120 ℃, reacts 8 hours, obtains containing the organic silicon surfactant product of glycosyl, and recording its surface tension is 21.1mN/m.
Claims (9)
1. organic silicon surfactant that contains glycosyl, the molecular structural formula of organic silicon surfactant that it is characterized in that containing glycosyl is following:
Wherein, R '=-CH
3Or R;
R does
X, y is 0～100 integer, is preferably 0～20; A is 0～20 integer, is preferably 0～4; B is 1～2.
When y=0, R ' can not be-CH entirely
3
2. a kind of organic silicon surfactant that contains glycosyl as claimed in claim 1 is characterized in that x, and y is 0～20.
3. a kind of organic silicon surfactant that contains glycosyl as claimed in claim 1 is characterized in that a is 0～4.
4. a kind of preparation method who contains the organic silicon surfactant of glycosyl as claimed in claim 1, the reaction temperature that it is characterized in that allyl alcohol or allyl ether and glucose is 80～120 ℃.
5. a kind of preparation method who contains the organic silicon surfactant of glycosyl as claimed in claim 1, the mole proportioning that it is characterized in that allyl alcohol or allyl ether and glucose is 4～8: 1.
6. a kind of preparation method who contains the organic silicon surfactant of glycosyl as claimed in claim 1; It is characterized in that the required catalyst of allyl alcohol or allyl ether and glucose response is a p-methyl benzenesulfonic acid, its mole dosage is a catalyst: glucose=1～10: 100.
7. a kind of preparation method who contains the organic silicon surfactant of glycosyl as claimed in claim 1, the reaction temperature that it is characterized in that pi-allyl glucosides and containing hydrogen silicone oil is 80～120 ℃.
8. a kind of preparation method who contains the organic silicon surfactant of glycosyl as claimed in claim 1, the mole proportioning that it is characterized in that si-h bond in pi-allyl glucosides and the containing hydrogen silicone oil is 1～1.1: 1.
9. a kind of preparation method who contains the organic silicon surfactant of glycosyl as claimed in claim 1 is characterized in that it is chloroplatinic acid that pi-allyl glucosides and containing hydrogen silicone oil react required catalyst, and its mole dosage is a chloroplatinic acid: si-h bond=1～10: 100000.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110402482XA CN102513027A (en) | 2011-12-07 | 2011-12-07 | Method for preparing organosilicon surfactant containing glucoside group |
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|---|---|---|---|
| CN201110402482XA CN102513027A (en) | 2011-12-07 | 2011-12-07 | Method for preparing organosilicon surfactant containing glucoside group |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105829405A (en) * | 2013-12-17 | 2016-08-03 | 瓦克化学股份公司 | Polyorganosiloxane gels having glycoside groups |
| CN109054021A (en) * | 2018-07-06 | 2018-12-21 | 福建拓烯新材料科技有限公司 | A kind of preparation method of sugar modified polyorganosiloxane |
| CN111991744A (en) * | 2020-08-19 | 2020-11-27 | 西南石油大学 | Environment-friendly fluorine-free foam extinguishing agent and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3389160A (en) * | 1964-07-14 | 1968-06-18 | Union Carbide Corp | Dialkylamino hydroxy organosilicon compounds and derivatives thereof |
| US5428142A (en) * | 1993-10-20 | 1995-06-27 | Siltech Inc. | Silicone based glycosides |
| FR2753901A1 (en) * | 1996-09-30 | 1998-04-03 | Oreal | USE OF A GLUCOSID GROUPED POLYDIMETHYLSILOXANE AS A MOISTURIZING AGENT IN A COSMETIC OR DERMATOLOGICAL COMPOSITION |
| CN101690878A (en) * | 2009-10-13 | 2010-04-07 | 广州天赐有机硅科技有限公司 | Method for manufacturing organosilicon surfactant with T-shaped structure for pesticide |
-
2011
- 2011-12-07 CN CN201110402482XA patent/CN102513027A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3389160A (en) * | 1964-07-14 | 1968-06-18 | Union Carbide Corp | Dialkylamino hydroxy organosilicon compounds and derivatives thereof |
| US5428142A (en) * | 1993-10-20 | 1995-06-27 | Siltech Inc. | Silicone based glycosides |
| FR2753901A1 (en) * | 1996-09-30 | 1998-04-03 | Oreal | USE OF A GLUCOSID GROUPED POLYDIMETHYLSILOXANE AS A MOISTURIZING AGENT IN A COSMETIC OR DERMATOLOGICAL COMPOSITION |
| CN101690878A (en) * | 2009-10-13 | 2010-04-07 | 广州天赐有机硅科技有限公司 | Method for manufacturing organosilicon surfactant with T-shaped structure for pesticide |
Non-Patent Citations (1)
| Title |
|---|
| G.JONAS ET AL: "《Carbohydrate modified polysiloxanesⅡ.Synthesis via hydrosilation of mono-di- and oligosaccharide allylglycoside》", 《ACTA POLYMER》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105829405A (en) * | 2013-12-17 | 2016-08-03 | 瓦克化学股份公司 | Polyorganosiloxane gels having glycoside groups |
| CN105829405B (en) * | 2013-12-17 | 2018-09-18 | 瓦克化学股份公司 | Polysiloxane gel with glucosides group |
| CN109054021A (en) * | 2018-07-06 | 2018-12-21 | 福建拓烯新材料科技有限公司 | A kind of preparation method of sugar modified polyorganosiloxane |
| CN111991744A (en) * | 2020-08-19 | 2020-11-27 | 西南石油大学 | Environment-friendly fluorine-free foam extinguishing agent and preparation method thereof |
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Application publication date: 20120627 |