CN110479184A - A kind of agar glycosyl emulsifier and its preparation method and application - Google Patents
A kind of agar glycosyl emulsifier and its preparation method and application Download PDFInfo
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- CN110479184A CN110479184A CN201910717803.1A CN201910717803A CN110479184A CN 110479184 A CN110479184 A CN 110479184A CN 201910717803 A CN201910717803 A CN 201910717803A CN 110479184 A CN110479184 A CN 110479184A
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0036—Galactans; Derivatives thereof
- C08B37/0039—Agar; Agarose, i.e. D-galactose, 3,6-anhydro-D-galactose, methylated, sulfated, e.g. from the red algae Gelidium and Gracilaria; Agaropectin; Derivatives thereof, e.g. Sepharose, i.e. crosslinked agarose
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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Abstract
The present invention discloses a kind of agar glycosyl emulsifier, its raw material includes agarose and derivative of fatty acid, the molar ratio of the agarose and the derivative of fatty acid is 1:2~1:4, wherein for the mole of the agarose in terms of disaccharide unit, the derivative of fatty acid is chloroacetic chloride, propionyl chloride, butyl chloride, valeric chloride, caproyl chloride, caprylyl chloride, decanoyl chloride, lauroyl chloride, myristyl chloride, palmitoyl chloride or stearic acid chloride.The invention also discloses a kind of preparation methods of agar glycosyl emulsifier, and the esterification modification of agarose is realized using solvent method, and simple process is high-efficient, it is easy to accomplish industrialized production.The agar glycosyl emulsifier has potential application prospect in medicine, cosmetics and food service industry.
Description
Technical field
The present invention relates to emulsifier technical fields, and in particular to be a kind of agar glycosyl emulsifier and preparation method thereof and
Using.
Background technique
Emulsion is to be dispersed in composed heterogeneous system in continuous phase by one or more discontinuous substances.Mesh
Before, emulsion in food and beverage industries using more and more extensive, in addition to the preparation such as sausage, cured of conventional cooked meat product
Intestines, cream, salad flavouring liquid etc. need outside the use of emulsifier, many functional foods or additive, as nutrient,
Essence, pigment, antibacterial agent and health care product etc. are also formed as emulsion and are applied in food.For the cream for keeping product formation stable
Shape liquid, key are that the suitable emulsifier of selection.Emulsifier is usually surface reactive material, is mainly risen when forming emulsion
The effect crucial to two, it is possible, firstly, to promote the formation of emulsion, second, the stability of emulsion can be improved.Food work
There are many emulsifier in industry, are broadly divided into natural and chemical synthesis two major classes, including protein, polysaccharide, phosphatide and table
Face activating agent.However, leading to natural prodcuts or natural addition as demand of the consumer for foodsafety is more and more harsh
The demand of agent becomes larger.Therefore, numerous food product industry is just attempting to use naturally occurring emulsifying agent and is made to replace in traditional processing at present
Artificial synthesized surfactant.
Currently, obtaining extensive concern using natural polysaccharide as emulsifier, water phase can be largely entered since polysaccharide has
Hydrophilic radical, by steric hindrance effect can maintain emulsion stabilization, avoid creaming and aggregation.It is with polysaccharide
The emulsion of emulsifier preparation is metastable at a variety of environmental conditions (including pH, ionic strength and temperature).In food
In industry, Arabic gum is the natural polysaecharides emulsifier being most widely used, especially using more in beverage production.So
And Arabic gum forms stable emulsion and needs oil mutually relatively high (reaching 1 ︰ 1) with the ratio of water phase.Economically come
It sees, the problem of utilization rate for enhancing grease is polysaccharide emulsifier urgent need to resolve.
In recent years, with the fast development of biotechnology, agarose as a kind of natural polysaccharide material increasingly by
People concern, due to agarose have porosity, hydrophily, without the hydroxyl on charged group and polysaccharide chain in certain condition
The advantages that different aglucons can be coupled down, have been widely used for the fields such as food, bioengineering, medicine, pharmacy.However,
Since agarose does not have as amphipathic needed for surfactant, surface tension and interface can not be effectively reduced
Power is restricted in the application as microcapsule wall material and embedding lipophilic active substance.And in the research of our early periods
It was found that can make agarose if carrying out specific hydrophobic modification to the hydroxyl in agarose molecules structure while there is emulsibility
Energy and gelling performance, during preparing emulsion, it has been found that due to the introducing of long chain hydrophobic group, the steric hindrance of formation
Agar glycosyl emulsifier can be enable to be emulsified at high temperature, and be able to maintain high stability.In addition, according to agarose solidifying
The characteristics of tridimensional network can be formed when gluey state between strand, emulsion can be made to be limited in hydrogel network under cryogenic
In network, to prevent from flocculating and coalesce, while improving the stability of emulsion, emulsion can be made to be formed by changing temperature
Emulsion-type gel, this characteristic have good application in cosmetic field.Therefore, according to the high temperature of agar glycosyl emulsifier cream
Change this characteristic of low temperature gel, a kind of novel emulsification agent material certainly will be become, this is for widening agarose in medicine, change
Application in cosmetic and food has great importance.
In consideration of it, the present inventor carries out in-depth study to the above problem, there is this case generation then.
Summary of the invention
The purpose of the present invention is to provide a kind of agar glycosyl emulsifiers, have good emulsibility and emulsion stability.
The object of the invention is also to provide a kind of preparation method and applications of agar glycosyl emulsifier.
In order to achieve the above objectives, solution of the invention is:
A kind of agar glycosyl emulsifier, raw material include agarose and derivative of fatty acid, the agarose and the rouge
The molar ratio of pipecolic acid derivative is 1:2~1:4, wherein the mole of the agarose, in terms of disaccharide unit, the fatty acid spreads out
Biology is chloroacetic chloride, propionyl chloride, butyl chloride, valeric chloride, caproyl chloride, caprylyl chloride, decanoyl chloride, lauroyl chloride, myristyl chloride, palm fibre
Palmitic acid acyl chlorides or stearic acid chloride.
A kind of preparation method of agar glycosyl emulsifier, comprising the following steps:
Step 1 disperses agarose in pyridine solvent, is configured to the agarose that mass concentration is 10%~40% and suspends
Liquid, pyridine are used as catalyst, acid binding agent and solvent in the reaction system；
Step 2, under magnetic stirring, derivative of fatty acid is added dropwise in sepharose suspension, at 80~120 DEG C
The molar ratio of 1~3h of lower reaction, the agarose and the derivative of fatty acid is 1:2~1:4, wherein the mole of agarose
In terms of disaccharide unit；
Step 3 is reacted to which excessive ethyl alcohol after reaction, is added with terminating, and is filtered after standing, is then successively used ethyl alcohol
And deionized water washing filtering；
Step 4, finally by volumetric concentration be 40~60% ethyl alcohol mixed with the product being obtained by filtration, removed after rotating
Residual organic solvent obtains the agar glycosyl emulsifier after drying and crushing.
In step 1, the derivative of fatty acid be chloroacetic chloride, propionyl chloride, butyl chloride, valeric chloride, caproyl chloride, caprylyl chloride,
Decanoyl chloride, lauroyl chloride, myristyl chloride, palmitoyl chloride or stearic acid chloride.
In step 1, the mass concentration of the sepharose suspension is 20%.
In step 2, the molar ratio of the agarose and the derivative of fatty acid is 1:2.
In step 2, the temperature of the reaction is 80 DEG C, and the time of the reaction is 1h.
In step 3, the quality dosage of the ethyl alcohol is 4~10 times of agarose quality described in step 1, the standing
Time is 30~60min.
In step 4, the quality dosage of the ethyl alcohol is 4~10 times of agarose quality described in step 1.
Above-mentioned agar glycosyl emulsifier forms the emulsion and needs to be added oil phase and water in the application formed in emulsion
Phase, the oil is mutually and the volumetric usage ratio of the water phase is 1:5~1:10, and the quality dosage of the agar glycosyl emulsifier is
0.2%~1.2%, formed the emulsion condition be at 35 DEG C~85 DEG C, with high-speed shearing emulsion machine 15000~
3~5min is sheared under the speed of 30000r/min.
After adopting the above technical scheme, a kind of agar glycosyl emulsifier of the present invention, to the hydroxyl in agarose molecules structure
Specific esterification modification is carried out, the molecular structure of agarose is introduced using the hydrophobic fatty acids chain of different chain length as esterification substituent group
In (as shown in formula I), make agarose while being provided with hydrophilic group and hydrophobic long-chain so that agarose have as emulsification
It is amphipathic necessary to agent, the product of different emulsifiabilities can be obtained by the length and content that change hydrophobic fatty acids chain,
The more simple agarose of emulsifiability is significantly increased, and compared with the common emulsifier of food, which has
Temperature-responsive has stronger emulsifying capacity and emulsion stability at high temperature, its emulsion can be formed under cryogenic
Emulsion-type gel, emulsion be limited in agar glycosyl formation Weak Gels network structure under, reduce emulsion flocculation and
Therefore coalescence, has potential application prospect in cosmetic field to enhance the stability of emulsion.
A kind of preparation method of agar glycosyl emulsifier of the present invention, the esterification modification of agarose is realized using solvent method,
Simple process, it is high-efficient, it is easy to accomplish industrialized production.The agar glycosyl emulsifier of preparation method preparation is as a kind of function
Property agarose derivative, be the intensive processing and utilization of agarose, and the added value for improving agarose provides one and new thinks
Road.
The reaction equation of formula I agarose and derivative of fatty acid
A kind of agar glycosyl emulsifier of the present invention is applied in emulsion, oil is mutually and the volumetric usage ratio of water phase is 1:5
~1:10 greatly reduces the use of grease, improves the utilization rate of grease.
Specific embodiment
In order to further explain the technical solution of the present invention, being explained in detail below by specific embodiment the present invention
It states.
One, the preparation of agar glycosyl emulsifier
Embodiment 1
A kind of preparation method of agar glycosyl emulsifier, comprising the following steps:
Step 1 weighs 20g agarose (0.06M, in terms of disaccharide unit) and is scattered in pyridine solvent, and it is dense to be configured to quality
The sepharose suspension that degree is 20%；
Under step 2, the magnetic agitation that low whipping speed is 350rpm, 21.7g (0.12M) lauroyl chloride is added dropwise to
In sepharose suspension, 1h is reacted at 80 DEG C；
Step 3 is reacted to which 100mL ethyl alcohol after reaction, is added with terminating, and is filtered after standing 30min, is then successively used
Ethyl alcohol and deionized water washing filtering；
Step 4, finally by 100mL volumetric concentration be 50% ethyl alcohol mixed with the product being obtained by filtration, removed after rotating
Residual organic solvent is removed, dodecyl agar glycosyl emulsifier is obtained after drying and crushing.
Embodiment 2
A kind of preparation method of agar glycosyl emulsifier, comprising the following steps:
Step 1 weighs 20g agarose (0.06M, in terms of disaccharide unit) and is scattered in pyridine solvent, and it is dense to be configured to quality
The sepharose suspension that degree is 20%；
Under step 2, the magnetic agitation that low whipping speed is 350rpm, 28.4g (0.12M) palmitoyl chloride is added dropwise to
In sepharose suspension, 1h is reacted at 80 DEG C；
Step 3 is reacted to which 100mL ethyl alcohol after reaction, is added with terminating, and is filtered after standing 30min, is then successively used
Ethyl alcohol and deionized water washing filtering；
Step 4, finally by 100mL volumetric concentration be 50% ethyl alcohol mixed with the product being obtained by filtration, removed after rotating
Residual organic solvent is removed, cetyl agar glycosyl emulsifier is obtained after drying and crushing.
Embodiment 3
A kind of preparation method of agar glycosyl emulsifier, comprising the following steps:
Step 1 weighs 20g agarose (0.06M, in terms of disaccharide unit) and is scattered in pyridine solvent, and it is dense to be configured to quality
The sepharose suspension that degree is 20%；
Under step 2, the magnetic agitation that low whipping speed is 350rpm, 31.9g (0.12M) stearyl chloride is added dropwise to
In sepharose suspension, 1h is reacted at 80 DEG C；
Step 3 is reacted to which 100mL ethyl alcohol after reaction, is added with terminating, and is filtered after standing 30min, is then successively used
Ethyl alcohol and deionized water washing filtering；
Step 4, finally by 100mL volumetric concentration be 50% ethyl alcohol mixed with the product being obtained by filtration, removed after rotating
Residual organic solvent is removed, octadecyl agar glycosyl emulsifier is obtained after drying and crushing.
Embodiment 4
A kind of preparation method of agar glycosyl emulsifier, comprising the following steps:
Step 1 weighs 20g agarose (0.06M, in terms of disaccharide unit) and is scattered in pyridine solvent, and it is dense to be configured to quality
The sepharose suspension that degree is 20%；
Under step 2, the magnetic agitation that low whipping speed is 350rpm, 25.6g (0.24M) butyl chloride is added dropwise to fine jade
In lipolysaccharide suspension, 1h is reacted at 80 DEG C；
Step 3 is reacted to which 200mL ethyl alcohol after reaction, is added with terminating, and is filtered after standing 30min, is then successively used
Ethyl alcohol and deionized water washing filtering；
Step 4, finally by 200mL volumetric concentration be 50% ethyl alcohol mixed with the product being obtained by filtration, removed after rotating
Residual organic solvent is removed, butyl-agarose base emulsifier is obtained after drying and crushing.
Embodiment 5
A kind of preparation method of agar glycosyl emulsifier, comprising the following steps:
Step 1 weighs 20g agarose (0.06M, in terms of disaccharide unit) and is scattered in pyridine solvent, and it is dense to be configured to quality
The sepharose suspension that degree is 20%；
Under step 2, the magnetic agitation that low whipping speed is 350rpm, 32.2g (0.24M) caproyl chloride is added dropwise to fine jade
In lipolysaccharide suspension, 1h is reacted at 80 DEG C；
Step 3 is reacted to which 200mL ethyl alcohol after reaction, is added with terminating, and is filtered after standing 30min, is then successively used
Ethyl alcohol and deionized water washing filtering；
Step 4, finally by 200mL volumetric concentration be 50% ethyl alcohol mixed with the product being obtained by filtration, removed after rotating
Residual organic solvent is removed, hexyl agar glycosyl emulsifier is obtained after drying and crushing.
Embodiment 6
A kind of preparation method of agar glycosyl emulsifier, comprising the following steps:
Step 1 weighs 20g agarose (0.06M, in terms of disaccharide unit) and is scattered in pyridine solvent, and it is dense to be configured to quality
The sepharose suspension that degree is 20%；
Under step 2, the magnetic agitation that low whipping speed is 350rpm, 39.0g (0.24M) caprylyl chloride is added dropwise to fine jade
In lipolysaccharide suspension, 1h is reacted at 80 DEG C；
Step 3 is reacted to which 200mL ethyl alcohol after reaction, is added with terminating, and is filtered after standing 30min, is then successively used
Ethyl alcohol and deionized water washing filtering；
Step 4, finally by 200mL volumetric concentration be 50% ethyl alcohol mixed with the product being obtained by filtration, removed after rotating
Residual organic solvent is removed, octyl sepharose base emulsifier is obtained after drying and crushing.
Two, performance test:
1, test method
(1) test of degree of substitution (DS)
Precise 2.0g agar glycosyl emulsifier sample, is placed in 250mL iodine flask, and 25mL, 0.5mol/L is added
NaOH solution stirs 72h.It is titrated with the HCl standard solution of 0.5mol/L after 2 drop phenolphthalein are added dropwise, is disappeared until red again, record
The HCl standard solution volume V of consumption1, while blank control experiment is done with natural agar sugar, record the HCl standard solution of consumption
Volume V0.The degree of substitution of agar glycosyl emulsifier-OH is calculated as follows:
W%=[(V0- V1)×10-1× (M-17) × c]/m formula (1)
DS=162 × w%/(M- (M-1) × w%) formula (2)
In formula (1) and formula (2): w% is the mass fraction of the contained access group of hydroxyl in each disaccharide unit on agarose；
DS is the degree of substitution of agar glycosyl emulsifier；M be esterification substituent group (specifically refer to dodecyl, cetyl, octadecyl,
Butyl, hexyl and octyl) molecular weight；M is the quality (g) of agar glycosyl emulsifier.
(2) emulsifying capacity and emulsion stability measurement
Made sample agar glycosyl emulsifier 0.25g is weighed, 25mL deionized water is added, heating is made into 1.0% after dissolving
Agarose solution (water phase), mixed with 5mL soybean salad oil (oily phase), i.e., oil mutually and water phase volume ratio be 1:5, at 75 DEG C
3min is sheared under the speed of 15000r/min with high-speed shearing emulsion machine, 100 μ L of suction foot emulsion is added 10mL's
It in 0.1% sodium dodecyl sulfate solution, shakes up, using SDS solution as blank, the light absorption value under 500nm wavelength is surveyed, with the suction of 0h
Light value A0The emulsion stability (ESI) of the emulsibility EA of representative sample, sample are calculated by formula, and ESI numerical value is bigger to be illustrated to emulsify
Stability is good.
ESI=A0×ΔT/ΔA
In formula:
ESI-emulsion stability
A0- light absorption value；
Δ T-time difference 1h；
Extinction value difference in Δ A-Δ T.
(3) measurement of emulsion particle diameter
Multiple scattering effect in order to prevent, should be by the emulsion of agar glycosyl emulsifier and soybean salad oil preparation before measurement
100 times are diluted with deionized water, the sample after dilution measures its particle size (Z- using ZetasizesizerNanoZs90
Average), polydispersity coefficient (PDI), Instrument measuring wavelength 658nm, survey fixed time temperature and maintain 25 by 133 ° of scattering angle
± 1 DEG C, equilibration time 2min.
(4) measurement of surface tension and interfacial tension
Agar glycosyl emulsifier sample is configured to the solution that mass concentration is 1.0% (w/w) with deionized water, is used
Full-automatic surface tension instrument measurement surface tension of the solution to air of DCAT21 and the interfacial tension to oily phase.It is selected in experiment small
Number platinum piece (length 10mm, width 9.95mm, with a thickness of 0.2mm) measures.
After small size platinum piece is cleaned with deionized water first, then with alcolhol burner calcination (with horizontal plane at 45 degree of angles into
Row), until the change of small size platinum piece is micro- red, the time is 20~30 seconds, is hung up properly after cooling stand-by on instrument.In planchet
Middle addition measures liquid, dries planchet outer wall, is placed on hoistable platform, measures.
(5) measurement of gel strength
Made agar glycosyl emulsifier sample 0.25g is weighed, 25mL deionized water is added, heating is made into 1.0% after dissolving
Agarose solution (water phase), mixed with 5mL soybean salad oil (oily phase), i.e., oil mutually compared with water be 1:5,75 DEG C with high speed
Emulsification pretreatment machine shears 3min under the speed of 15000r/min, covers preservative film after the solidification to be cooled of the emulsion of formation, in
20 DEG C of placement 15h, then measure gel strength with gel strength measuring instrument, and measurement is averaged three times.
2, data
(1) performance for each agar glycosyl emulsifier sample being prepared
The performance of each agar glycosyl emulsifier sample of table 1
The performance test results are as shown in table 1, the results showed that can be obtained by the length and content that change hydrophobic fatty acids chain
The different product of degree of substitution is obtained, to obtain the product of different emulsifiabilities.The emulsion of formation energy when temperature is lower than 30 DEG C
Emulsion-type gel is formed, gel strength is 50~120g/cm2。
(2) performance comparison of each the agar glycosyl emulsifier sample and conventional emulsifier that are prepared
By the agar glycosyl emulsifier for the different carbon chain lengths being prepared in Examples 1 to 6, respectively with agarose (AG,
Control) and common emulsifier Tween20, Tween80, sucrose fatty ester (SFAE, HLB13), sucrose fatty ester (SFAE,
HLB15), gelatin (Gelatin), the emulsibility (EA) of glycerin monostearate (GM) and emulsion stability (ESI) are same dense
It is compared under the conditions of degree (1.0% agarose solution), as shown in table 2, the results showed that the agarose that the present invention is prepared
Base emulsifier shows preferable emulsifying capacity, but shows slightly insufficient compared with Tween20, Tween80 and sucrose fatty ester, but
Common emulsifier is apparently higher than in terms of emulsion stability.
The performance comparison of each agar glycosyl emulsifier sample and conventional emulsifier in 2 present invention of table
Above-described embodiment and non-limiting product form and style of the invention, the ordinary skill people of any technical field
The appropriate changes or modifications that member does it, all should be regarded as not departing from patent category of the invention.
Claims (9)
1. a kind of agar glycosyl emulsifier, it is characterised in that: the raw material of the agar glycosyl emulsifier includes agarose and fat
The molar ratio of acid derivative, the agarose and the derivative of fatty acid is 1:2~1:4, wherein mole of the agarose
For amount in terms of disaccharide unit, the derivative of fatty acid is chloroacetic chloride, propionyl chloride, butyl chloride, valeric chloride, caproyl chloride, caprylyl chloride, the last of the ten Heavenly stems
Acyl chlorides, lauroyl chloride, myristyl chloride, palmitoyl chloride or stearic acid chloride.
2. preparing a kind of preparation method of agar glycosyl emulsifier as described in claim 1, it is characterised in that: including following step
It is rapid:
Step 1 disperses agarose in pyridine solvent, is configured to the sepharose suspension that mass concentration is 10%~40%,
Pyridine is used as catalyst, acid binding agent and solvent in the reaction system；
Step 2, under magnetic stirring, derivative of fatty acid is added dropwise in sepharose suspension, anti-at 80~120 DEG C
1~3h is answered, the molar ratio of the agarose and the derivative of fatty acid is 1:2~1:4, and wherein the mole of agarose is with two
Sugared unit meter；
Step 3 is filtered to which excessive ethyl alcohol after reaction, is added to terminate reaction, after standing, then successively with ethyl alcohol and is gone
Ionized water washing filtering；
Step 4, finally by volumetric concentration be 40~60% ethyl alcohol mix with the product being obtained by filtration, after rotating removing remain
Organic solvent obtains the agar glycosyl emulsifier after drying and crushing.
3. a kind of preparation method of agar glycosyl emulsifier according to claim 2, it is characterised in that: described in step 1
Derivative of fatty acid is chloroacetic chloride, propionyl chloride, butyl chloride, valeric chloride, caproyl chloride, caprylyl chloride, decanoyl chloride, lauroyl chloride, Pork and beans
Cool acyl chlorides, palmitoyl chloride or stearic acid chloride.
4. a kind of preparation method of agar glycosyl emulsifier according to claim 2, it is characterised in that: described in step 1
The mass concentration of sepharose suspension is 20%.
5. a kind of preparation method of agar glycosyl emulsifier according to claim 2, it is characterised in that: described in step 2
The molar ratio of agarose and the derivative of fatty acid is 1:2.
6. a kind of preparation method of agar glycosyl emulsifier according to claim 2, it is characterised in that: described in step 2
The temperature of reaction is 80 DEG C, and the time of the reaction is 1h.
7. a kind of preparation method of agar glycosyl emulsifier according to claim 2, it is characterised in that: described in step 3
The quality dosage of ethyl alcohol is 4~10 times of agarose quality described in step 1, and the time of the standing is 30~60min.
8. a kind of preparation method of agar glycosyl emulsifier according to claim 2, it is characterised in that: described in step 4
The quality dosage of ethyl alcohol is 4~10 times of agarose quality described in step 1.
9. a kind of agar glycosyl emulsifier according to claim 1 is in the application formed in emulsion, it is characterised in that: shape
Need to be added oil phase and water phase at the emulsion, the oil is mutually and the volumetric usage ratio of the water phase is 1:5~1:10, described
The quality dosage of agar glycosyl emulsifier be 0.2%~1.2%, formed the emulsion condition be at 35 DEG C~85 DEG C,
3~5min is sheared under the speed of 15000~30000r/min with high-speed shearing emulsion machine.
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