CN107955045A - Alkyl glycosides alkyl acid monoester sulfosalt surfactant and preparation method thereof - Google Patents
Alkyl glycosides alkyl acid monoester sulfosalt surfactant and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to a kind of alkyl glycosides alkyl acid monoester sulfosalt surfactant being shown below and preparation method thereof.The preparation method of the surfactant is as follows：After activating alkyl glycosides with alkaline matter, alkenyl succinic anhydride is added thereto and carries out esterification, then adds sulfonating agent aqueous solution, it is sulfonated to obtain alkyl glycosides alkyl monoesters sulfonate.The preparation method technique of the present invention is simple, and reaction temperature is low, energy saving easily-controllable.The surfactant had both had the performance of alkyl glycosides, it may have the characteristic of alkylsulfonate, foaming characteristic reduce, and there is stronger emulsifying ability, solve normal alkyl glucosides poorly water-soluble, the problem of alkylsulfonate alkali resistance is low, and it is resistant to the soda bath of 150g/L.
Description
Technical field
The invention belongs to synthesis of surfactant field, and in particular to a kind of alkyl glycosides alkyl acid monoester sulfonate
Surfactant and preparation method thereof.
Background technology
Alkyl glycosides (APG) in 1893 first by German Emil Fischer synthesize, until the 1980s with
Paid attention to successively by major company both domestic and external (such as P＆G, Henkel, flower king) and colleges and universities afterwards and it is researched and developed.Alkyl sugar
Glycosides is formed by fatty alcohol and glucose condensation, has the characteristic of two kinds of surfactants of nonionic and anion, spumescence
Energy, detergency, compatibility are excellent, and nontoxic, easily biological-degradable, are a kind of more environmentally friendly surfactants.It is but long
Alkyl group glucosides it is water-soluble poor, in order to overcome this defect, in alkyl glycosides introduce alkyl acid monoester sulfonate,
Prepare a kind of new nonionic surfactant --- alkyl glycosides alkyl acid monoester sulfonate.Alkyl acid monoester sulphur
The introducing of hydrochlorate so that such surfactant had not only had the characteristic of alkyl glycosides, but also the characteristic with alkylsulfonate, at the same time
What also the introducing with succinate also increased surfactant goes oiliness.In addition, under basic conditions, the glucose in molecule
The deionization of glycosides part, makes its negatively charged, intermolecular mutually exclusive, stability increase, so that the alkali resistance to alkylsulfonate
Haveing a certain upgrade property, while the introducing of sulfonate anionic adds the water solubility of alkyl glycosides, the introducing of chain alkyl can
So that the foaming characteristic of surfactant has declined.Therefore the surfactant can be applied to the industries such as daily use chemicals, weaving, especially
Suitable for the pre-treatment of textile.
According to the literature, the sulphosuccinates of alkyl glycosides are modified, and usually alkyl glycosides and maleic anhydride are through ester
After changing reaction, then sulfonating reaction is carried out, alkyl glycosides sulfosuccinate ester salt is prepared, such as document " alkyl polyglycoside sulfosuccinic acid
The synthesis of monoester disodium salt " (Guizhou University of Technology's journal (natural science edition), 2006, Vol.36No.5), " starch alkyl polyglycoside
The synthesis of sulfosuccinic acid ester sodium salt and performance study " (chemical science and technology, 2010, Vol.18No.1) and patent
CN103864863A.In addition patent CN106459121A is the effect of alkyl glycosides and itaconic acid or itaconic anhydride in catalyst
Under, alkyl glycosides itaconate is obtained, then by sulfonating reaction, obtains alkyl glycosides sulfomethvl succinate.Patent
CN103623744A is maleic anhydride with after Isosorbide-5-Nitrae butanediol single-esterification, then with alkyl glycosides reacting generation double esterification product,
Generation Alkyl glycoside dimeric surfactant after sulfonated.It is prepared by the butanedioic acid sulfonate of the alkyl glycosides described in document above
By the use of the larger organic solvent of toxicity (such as N-N dimethylformamides, toluene, chlorobenzene) as solvent in journey, reaction temperature is higher,
More than 90 DEG C.And for using alkenyl succinic anhydride as esterifying agent, esterification occurs with alkyl glycosides, prepare and have by sulfonation
Have the sulfosuccinate monoeaster surfactant of alkyl, and preparation method thereof do not have document report mistake also.Alkenyl succinic anhydride
For a kind of very strong nucleopilic reagent of activity, nucleophilic substitution occurs with alkyl glycosides, reaction is irreversible, and 30~60
It can complete to react in the range of DEG C, reaction is simple, easily operated.
Therefore, alkyl glycosides alkyl acid monoester sulfosalt surfactant of the invention and preparation method thereof, has
Important realistic meaning and application value.
The content of the invention
It is an object of the present invention to provide a kind of alkyl glycosides alkyl acid monoester sulfosalt surfactant and
Its preparation method.
The chemical structural formula of alkyl glycosides alkyl acid monoester sulfonate of the present invention is：
Wherein R1For C6~C10Straight or branched alkane；
R2For C6~C18Straight or branched alkyl；
N is 1~5；
M is Na, K or NH4 +Or their mixture.
The molecular weight of the alkyl glycosides alkyl acid monoester sulfonate is preferably 600~3000.
The preparation method of alkyl glycosides alkyl sulfosuccinic monoesters sulfonate of the present invention comprises the following steps：
Step 1: using the aqueous solution of alcohol as solvent, alkyl glycosides is dissolved, adding alkaline matter at 30~40 DEG C lives
Change, 0.5~2h of activation obtains middle system A；
Step 2: adding alkenyl succinic anhydride into above-mentioned intermediate system A, carry out being esterified under the conditions of 30~60 DEG C anti-
Should, pH is adjusted in reaction process and is maintained between 8.0~10.0, pH to 6~7 is adjusted after reacting 2~4h, obtains middle system B；
Step 3: adding sulfonating agent aqueous solution into above-mentioned intermediate system B, 2~3h is reacted under the conditions of 70~80 DEG C, is obtained
Alkyl glycosides alkyl sulfonic acid base monomester succinate.
The alkyl glycosides alkyl acid monoester sulfosalt surfactant of the present invention has alkyl glycosides and alkyl sulfonic acid concurrently
The characteristic of salt, has excellent surface-active, can solve normal alkyl glucosides poorly water-soluble, and alkylsulfonate alkali resistance is low to ask
Topic, and it is resistant to the soda bath of 150g/L.
Brief description of the drawings
Fig. 1 is the infared spectrum for the alkyl glycosides alkyl sulfosuccinic monoesters sulfonate that embodiment 1 obtains.
Fig. 2 is the infared spectrum for the alkyl glycosides alkyl sulfosuccinic monoesters sulfonate that embodiment 2 obtains.
Embodiment
In one preferred embodiment, a kind of alkyl glycosides alkyl sulfosuccinic monoesters sulfonate table of the invention
The chemical structural formula of face activating agent is：
Wherein R1For C6~C10Straight or branched alkane, more preferably C6、C7、C8、C10Linear paraffin；
R2For C6~C18Straight or branched alkyl, be more optimized for C8~C14Straight or branched alkyl；
N is 1~5, more preferably 1~2；
M is Na, K or NH4 +Or their mixture.
The molecular weight of the alkyl glycosides alkyl acid monoester sulfonate is preferably such as 600~3000, more preferably
For 800~1800.
In one preferred embodiment, above-mentioned a kind of alkyl glycosides alkyl sulfosuccinic monoesters sulphonate surface
The preparation method of activating agent comprises the following steps：
Step 1: using the aqueous solution of alcohol as solvent, alkyl glycosides is dissolved, adding alkaline matter at 30~40 DEG C lives
Change, 0.5~2h of activation obtains middle system A；
Step 2: adding alkenyl succinic anhydride into above-mentioned intermediate system A, carry out being esterified under the conditions of 30~60 DEG C anti-
Should, adjusted in reaction process with the alkaline substance solution of 4~5wt% between pH is maintained at 8.0~10.0, after 2~4h of reaction
PH to 6~7 is adjusted with the hydrochloric acid solution of 4~5wt%, obtains middle system B；
Step 3: adding sulfonating agent aqueous solution into above-mentioned intermediate system B, 2~3h is reacted under the conditions of 70~80 DEG C, is obtained
Alkyl glycosides alkyl sulfonic acid base monomester succinate.
Step 4: solvent is recovered under reduced pressure, light brown paste product is obtained after washed, separating-purifying.
In alkaline conditions, the hydroxyl on alkyl polyglycoside molecule exposes negative oxygen ion active group, nucleopilic reagent alkenyl
The anhydride rings of succinic anhydride are opened, and the ester bond of one end is combined with negative oxygen ion, and other end generation carboxylate, which is can not
Inverse, then sulfonate is introduced after sulfonated reaction, the alkyl glycosides alkyl acid monoester sulfonate of generation is a kind of hydrophilic group
Group and parents' molecule of lipophilic group composition, have unique molecular structure, there is excellent surface-active, have biodegradation
Property.
In one preferred embodiment, above-mentioned steps one, the alkaline matter used in step 2 be sodium hydroxide, hydrogen-oxygen
Change one or several kinds of mixtures of potassium, sodium carbonate or potassium carbonate.
In one preferred embodiment, above-mentioned steps one, the alcohol used in step 2 be water miscible isopropanol, positive fourth
One or more of mixtures of alcohol, sec-amyl alcohol etc..
In one preferred embodiment, the alkyl glycosides used in above-mentioned steps one includes C6~C18Straight chain or with branch
The alkyl glycosides of chain, molecular weight are, for example, 250~800, are preferably C8~C12Straight chain or branched alkyl glycosides, molecular weight
For example, 300~600.
In one preferred embodiment, in the aqueous solution of the alcohol used in above-mentioned steps one, the mass ratio of alcohol and water is
1:0.1~0.5, more preferably 1:0.2~0.4.
In one preferred embodiment, the alkenyl succinic anhydride used in above-mentioned steps two includes C8~C12Alkenyl amber
Amber acid anhydrides, is more optimized for octenyl succinic acid anhydride (OSA), nonenyl succinic acid acid anhydride (NSA), dodecenylsuccinic anhydride (DDSA)
Deng.
In one preferred embodiment, the sulfonating agent used in above-mentioned steps three is sodium salt, sylvite, the ammonium salt of sulfurous acid
Or their mixture.
In one preferred embodiment, the alkyl glycosides and the molar ratio of alkenyl succinic anhydride are 1:1.0~
1.5, more preferably 1:1.0~1.2.
In one preferred embodiment, the molar ratio 1.1~1.5 of the sulfonating agent and alkenyl succinic anhydride:1,
More preferably 1.1~1.3:1.
The applicant carries out innovation modification to alkyl glycosides, and alkyl acid monoester sulfonate is introduced in alkyl glycosides,
Prepare a kind of alkyl glycosides alkyl acid monoester sulfosalt surfactant.The surfactant has the advantage that：One side
Face introduces water miscible sulfonate anionic and promotes the water solubility of alkyl glycosides, while can increase its stability in hard water；It is another
Aspect, what the introducing of succinate can increase novel surfactant goes oiliness；Another further aspect, the introducing of alkyl glycosides, at the same time
To haveing a certain upgrade property of alkylsulfonate alkali resistance.The novel surfactant integrates the excellent of alkyl glycosides and alkylsulfonate
Gesture, while their own deficiency is overcome, there is the strong characteristic of low bubble, emulsifying ability, can be applied to the row such as daily use chemicals, weaving
Industry, especially suitable for Pretreatment of textile.
Embodiment
With reference to specific embodiment, the present invention is further explained.It is to be understood that these embodiments are merely to illustrate the present invention
Rather than limit the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, people in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Scope.
Raw material in following embodiment is commercially available.Experimental data is measured according to following method in following embodiment：
1) molecular weight determination：Measured using HLC-8320GPC types gel permeation chromatograph (Japanese TOSOH Co., Ltd), 25
DEG C when mobile phase be DMF, reference is used as using polymethyl methacrylate (PMMA).
2) foaming characteristic of surfactant：Roche blistering instrument method measured concentration is used to exist for the surfactant solution of 1g/L
Frothing capacity under the conditions of 60 DEG C, foam height is the foaming power of the surfactant when solution stops, and foam height is more raised
Bubble power is bigger, and the ratio of foam height and foam height during cutout is foam stability after 5min, and ratio is high, illustrates that the surface is lived
The foam stability of property agent is better.
3) emulsifying ability of surfactant：Has the surfactant water that 40ml 2g/L are sequentially added in plug graduated cylinder in 100mL
Solution, then adds 40mL oil (atoleine, white oil etc.), covers plug.To have the hand filled in graduated cylinder and be clamped in vertical oscillation device
On handle, machine is opened, with 5 grades of velocity fluctuation 10 times, standing 1min, then repeats, 6 times altogether, vibrates finishes for the last time
Graduated cylinder is stood on testing stand afterwards, starts timing, observes and records time when graduated cylinder bottom separates 10mL water, time longer emulsification
Power is better.
4) alkali resistance is tested：
Formula
Surfactant 15g/L
NaOH xg/L
When more than configuration the working solution room temperature 4 of formula is small, observe in working solution floating oil, floccule, band whether occur
The wild effect such as shape muddiness or precipitation.
Embodiment 1
By alkyl glycosides APG0810 (Jiangsu Wan Qi bio tech ltd, solid content 50%) 32g in the present embodiment
(0.05mol) and 32ml isopropanols are added in four-hole boiling flask, and NaOH 2.4g (0.06mol) are added at 35 DEG C, are lived
Change, add octenyl succinic acid anhydride (Nanjing Gutian chemical industry) 12.5g (0.06mol) after activating 1h, react, reacting at 35 DEG C
During be maintained at 8.0~8.5 with the pH value of the NaOH aqueous conditions systems of 4~5wt% between, react after 3h with 4~
The hydrochloric acid solution of 5wt% adjusts pH to 6~7.Then the NaHSO of 37.5g 20wt% (0.072mol) is added3Aqueous solution, 80
2h is reacted under the conditions of DEG C, obtains alkyl glycosides alkyl acid monoester sulfonate crude product.Solvent, washed, separation is recovered under reduced pressure
Light brown paste product S1 is obtained after purification.
Infrared test is carried out to obtained product S1, from figure 1 it appears that 1180cm-1It is neighbouring it is bimodal be different C-O
With-SO3The vibration peak of overlapping generation, 1731cm-1For the stretching vibration peak of C=O, 1039cm-1, 1034cm-1For the flexible of C-O
Vibration peak, illustrates the formation for having ester；2975cm-1、2933cm-1、2883cm-1、1478cm-1Annex is-CH3、-CH2Vibration
Peak, 724cm-1Annex is CH2The deformation vibration peak of C-H in long-chain, illustrates that there are C-H long-chains in molecule.3400cm-1Annex is O-
H stretching vibration peaks, it was demonstrated that product is alkyl glycosides alkyl acid monoester sulfonate.HLC-8320GPC type gel permeation chromatographies
Instrument tests the molecular weight of product as 974.
Embodiment 2
By alkyl glycosides APG0810 (Jiangsu Wan Qi bio tech ltd, solid content 50%) 64g in the present embodiment
(0.10mol) and 64ml isopropanols are added in four-hole boiling flask, and NaOH 4.8g (0.12mol) are added at 35 DEG C, are lived
Change, add dodecenylsuccinic anhydride (Nanjing Gutian chemical industry) 32g (0.12mol) after activating 1h, react, reacting at 45 DEG C
During with the pH value of the NaOH aqueous conditions systems of 4~5wt%, be maintained between 8.0~8.5, react after 3h with 4~
The hydrochloric acid solution of 5wt% adjusts pH to 6~7.Then the NaHSO of 75.0g 20wt% (0.144mol) is added3Aqueous solution, 85
2h is reacted under the conditions of DEG C, obtains alkyl glycosides alkyl acid monoester sulfonate crude product.It is recovered under reduced pressure solvent, product is washed,
Light brown paste product S2 is obtained after separating-purifying.Infrared test is carried out to obtained product S2, from figure 2 it can be seen that
1180cm-1It is neighbouring bimodal for different C-O and-SO3The vibration peak of overlapping generation, 1731cm-1For the stretching vibration peak of C=O,
1039cm-1, 1034cm-1For the stretching vibration peak of C-O, illustrate the formation for having ester；2975cm-1、2933cm-1、2883cm-1、
1478cm-1Annex is-CH3、-CH2Vibration peak, 724cm-1Annex is CH2The deformation vibration peak of C-H, illustrates molecule in long-chain
In there are C-H long-chains；3400cm-1Annex is O-H stretching vibration peaks, it was demonstrated that product is alkyl glycosides alkyl acid monoester sulfonic acid
Salt.HLC-8320GPC type gel permeation chromatographs test the molecular weight of product as 1032.
Embodiment 3
Blistering of the present embodiment to alkyl glycosides alkyl acid monoester sulfosalt surfactant made from embodiment 1,2
Property, emulsifying ability, alkali resistance are tested, and test result is shown in Table 1, table 2.
Table 1
| Surfactants Name | Foaming characteristic/cm | Foam stability |
| S1 | 6.2 | 0.83 |
| S2 | 4.8 | 0.88 |
| SAS60 | 15.5 | 0.30 |
| APG0810 | 13.8 | 0.94 |
Table 2
Note：SAS60 (sodium secondary alkyl sulfonate, Clariant) in table 1,2, APG0810 (alkyl glycosides, Jiangsu Wan Qi biologies
Science and Technology Ltd., solid content 50%).
Table 3
By table 1 find out the alkyl glycosides alkyl acid monoester sulfonate for preparing of the present invention have it is opposite with SAS60,
Foaming characteristic relatively low APG0810, good foam stability.Longer with access alkyl carbon chain, foaming characteristic is lower, foam stability
It is higher.Know that their emulsifying ability is better than SAS60 and APG0810 by table 2.In addition table 3 illustrates the alkyl glycosides alkyl succinic acid
Monoesters sulfosalt surfactant is stablized in the soda bath of 150g/L.
Claims (10)
1. a kind of alkyl glycosides alkyl acid monoester sulfosalt surfactant, its chemical structural formula are：
Wherein R1For C6~C10Straight or branched alkane；
R2For C6~C18Straight or branched alkyl；
N is 1~5；
M is Na, K or NH4 +Or their mixture.
2. a kind of preparation method of alkyl glycosides alkyl monoesters sulfosalt surfactant according to claim 1,
It is characterized in that, the preparation method comprises the following steps：
Step 1: using the aqueous solution of alcohol as solvent, alkyl glycosides is dissolved, adding alkaline matter at 30~40 DEG C is activated,
Obtain middle system A；
Step 2: adding alkenyl succinic anhydride into above-mentioned intermediate system A, esterification is carried out under the conditions of 30~60 DEG C, instead
PH is adjusted during answering to be maintained between 8.0~10.0, is adjusted pH to 6~7 after reacting 2~4h, is obtained middle system B；
Step 3: adding sulfonating agent aqueous solution into above-mentioned intermediate system B, 2~3h is reacted under the conditions of 70~80 DEG C, obtains alkyl
Glucosides alkyl monoesters sulfonate,
3. preparation method according to claim 2, wherein Step 1: the alkaline matter described in step 2 is hydroxide
Sodium, potassium hydroxide, one or several kinds of mixtures of sodium carbonate or potassium carbonate.
4. preparation method according to claim 2, the alcohol wherein described in step 1 is water miscible isopropanol, positive fourth
Alcohol, sec-amyl alcohol or their mixture.
5. the alkyl glycosides described in preparation method according to claim 2, wherein step 1 includes C6~C18Straight chain or
Branched alkyl glycosides.
6. in the aqueous solution of the alcohol described in preparation method according to claim 2, wherein step 1, the mass ratio of alcohol and water
For 1:0.1~0.5.
7. the alkenyl succinic anhydride described in preparation method according to claim 2, wherein step 2 includes C8~C12Alkene
Base succinic anhydride.
8. sulfonating agent described in preparation method according to claim 2, wherein step 3 is the sodium salt of sulfurous acid, sylvite,
Ammonium salt or their mixture.
9. preparation method according to claim 2, wherein the alkyl glycosides and the molar ratio of alkenyl succinic anhydride are
1:1.0~1.4.
10. preparation method according to claim 2, wherein the sulfonating agent and the molar ratio 1.1 of alkenyl succinic anhydride
~1.5：1.
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