CN108837773A - A kind of viscoelastic solution formed by abietyl dipeptides surfactant - Google Patents
A kind of viscoelastic solution formed by abietyl dipeptides surfactant Download PDFInfo
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- CN108837773A CN108837773A CN201810636967.7A CN201810636967A CN108837773A CN 108837773 A CN108837773 A CN 108837773A CN 201810636967 A CN201810636967 A CN 201810636967A CN 108837773 A CN108837773 A CN 108837773A
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
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- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Abstract
The invention discloses a kind of viscoelastic solution formed by abietyl dipeptides surfactant, belong to the synthesis and application field of natural products surfactant.The present invention, which has been synthesized a kind of abietyl dipeptides surfactant R -11-2-Na and compounded the surfactant (R-11-2-Na) with certain proportion with choline chloride (ChCl) to be formed, has good viscoelastic solution.The concentration of surfactant of the invention is in 140-300mmolL‑1When, the stability of viscoelastic solution is preferable, which can be applied to the industrial process such as household chemicals formula and oil exploitation.
Description
Technical field
The present invention relates to a kind of viscoelastic solution formed by abietyl dipeptides surfactant, and it is living to belong to natural products surface
The synthesis and application field of property agent.
Background technique
The viscoelastic solution that surfactant is formed shows in fields such as personal care articles, oil field fracturing fluid, fluid drag-reduction agent
Broad application prospect out.Surfactant viscoelastic solution is mainly by surfactant asymmetric aggregation formed in solution
Structure is cross-linked with each other and is formed, and not only needs suitable concentration and temperature, it is also necessary to suitable surfactant molecule structure.?
In viscoelastic solution system involved in studying at present, the overwhelming majority is all the system that cationic surfactant is formed, by yin
The viscoelastic micelle volume that ionic surface active agent is constructed is then more rare.However, being used for the system that cation is constructed
The advantages of viscoelastic solution constructed based on anionic surfactant, is also clearly.Anionic surfactant usually has
Have better biological degradability and lower toxicity, can be applicable to many cationic surfactants be not suitable for using field,
Such as tertiary oil recovery, daily necessities and food processing.In addition, as the idea of " Green Chemistry " is rooted in the hearts of the people, traditional petroleum
Chemical product has no longer adapted to the theory of modern society's health environment-friendly.
Characteristic and important forest resourceies of the rosin as China have reproducibility, biodegradable, cheap
The advantages that, abundance.Rosin acid with tricyclic diterpene structure is the main component of rosin, this by 20 carbon atom groups
At rigid-skeleton show apparent hydrophobicity.The structure may be incorporated into other substituent groups or active group, be easy to
Synthesize multiple target compounds.Amino acid also has many advantages, such as that renewable, biodegradable, abundance, structure are easy to modify,
It is the important raw material sources of green surfactant.Anionic rosin base amino is obtained using rosin and amino acid as Material synthesis
Acid surfaces activating agent, and be used to construct surfactant viscoelastic solution, meet the design concept of " environmentally protective ", meets and work as this life
The development trend of boundary's surfactant industry.
Summary of the invention
The purpose of the present invention is by serial reaction, dividing using the main component dehydroabietic acid in disproportionated rosin as raw material
Amino acid dipeptide unit is introduced in sub, synthesizes a kind of abietyl dipeptides surfactant.And based on this surfactant,
Choline chloride is added to construct a kind of stable viscoelastic solution.
The first purpose of the invention is to provide a kind of abietyl dipeptides surfactant (R-11-2-Na), structural formulas
It is as follows：
Wherein, M is alkali metal, can be Na or K.
In one embodiment, the abietyl dipeptides surfactant is with the main component dehydrogenation in disproportionated rosin
Abietic acid is Material synthesis.
In one embodiment, the synthetic route of the abietyl dipeptides surfactant is as follows：
In one embodiment, the Na can be substituted with K.
A second object of the present invention is to provide a kind of viscoelastic solution, the viscoelastic solution is based on abietyl dipeptides surface
The viscoelastic solution of activating agent (R-11-2-Na).
In one embodiment, the viscoelastic solution is by abietyl dipeptides surfactant and chlorination gallbladder of the invention
Alkali (ChCl) aqueous solution is mixed to get.
In one embodiment, the molar ratio of the abietyl dipeptides surfactant and choline chloride is 1:1.
In one embodiment, the viscoelastic solution, in R-11-2-Na/ChCl system, abietyl dipeptides surface-active
The concentration range of agent is 140-300mmolL-1。
Third object of the present invention is to provide answering for the abietyl dipeptides surfactant or the viscoelastic solution
With.
In one embodiment, the application includes for personal care articles, oil field fracturing fluid, fluid drag-reduction agent etc..
Beneficial effect
(1) present invention, by serial reaction step, synthesizes a kind of point using the important derivatives dehydroabietic acid of rosin as raw material
Son includes the anionic rosin based surfactants R-11-2-Na of two peptide units.The surfactant has preferable aggregation
Ability, critical micelle concentration value are 0.23mmolL-1。
(2) choline chloride is added into surfactant R -11-2-Na solution, a kind of fabulous molten of viscoplasticity can be formed
Liquid；After adding organic salt choline chloride (ChCl) into the aqueous solution of R-11-2-Na, it is molten to be capable of forming a kind of stable viscoelastic
Liquid, the zero-shear viscosity of R-11-2-Na/ChCl system is up to 1 × 103Pas, be rosin novel surfactant synthesis and
The application of new technical field lays the foundation.Meanwhile additive choline chloride is as a kind of edible water soluble vitamin product,
Equally there is environmentally protective feature, the viscoelastic solution formed by the two is in fields such as food additives, cosmetics, tertiary oil recoveries
It is with a wide range of applications.The R-11-2-Na that Na is replaced using K, also there is similar effect.
Detailed description of the invention
Fig. 1 abietyl dipeptides surfactant R -11-2-Na's1H NMR。
The surface tension γ of Fig. 2 abietyl dipeptides surfactant R -11-2-Na with concentration C change curve (25
℃)。
Viscosity of Fig. 3 viscoelastic solution R-11-2-Na/ChCl system under various concentration with shear rate variation (25
℃)。
Elasticity modulus (G ') and viscous modulus (G ") of Fig. 4 viscoelastic solution R-11-2-Na/ChCl system under various concentration
With the variation (25 DEG C) of angular frequency (ω).
Specific embodiment
The synthetic route of abietyl dipeptides surfactant of the invention is as follows：
Embodiment 1：The synthesis of compound 1
11- aminoundecanoic acid (20.1g, 0.10mol) and methanol (32.0g, 1.00mol) are mixed and are placed in tri- neck of 500mL
In bottle.Thionyl chloride (14.3g, 0.12mol) is slowly added dropwise at 0 DEG C, after completion of dropwise addition, the reaction was continued 1h.It flows back at 70 DEG C
Reaction to no gas generates.Methanol is removed under reduced pressure.Obtained thick liquid is recrystallized three times with methanol/ethyl acetate, is filtered
To white solid be compound 1.
Embodiment 2：The synthesis of compound 2
By the dichloromethane solution of compound 1 (30.2g, 0.12mol), triethylamine (44.5g, 0.44mol), dehydroabietic acid
(30.0g, 0.10mol) and HATU (41.8g, 0.11mol) mixing are placed in 500mL three-necked bottle, and appropriate 4- diformazan ammonia is added
Yl pyridines react 1h at 35 DEG C as catalyst.Water is added into mixture, is extracted with dichloromethane, organic layer is washed with water
It is 5-6 times, then dry with anhydrous magnesium sulfate.After suction filtration, filtrate removes solvent under reduced pressure.With silica gel column chromatography purified product
(eluant, eluent is petroleum ether：Ethyl acetate=4:1) the faint yellow viscous liquid, obtained is compound 2, yield：85%.
Embodiment 3：The synthesis of compound 3
The ethyl alcohol and 0.4g water of NaOH (2g, 0.05mol), 80mL are added into the single port bottle of 250mL, stirs complete to NaOH
Fully dissolved adds compound 2 (24.9g, 0.05mol), reacts 3h at 70 DEG C.After completion of the reaction, solvent is removed under reduced pressure, obtains
To white solid.Gained white solid (40g, 0.092mol) is soluble in water, and dense HCl, which is added, makes solution in acidity.Use acetic acid
Ethyl ester extraction, organic layer are washed with water 5-6 times, dry with anhydrous magnesium sulfate, filter, and filtrate decompression removes solvent, obtain compound
3.Yield：89%.
Embodiment 4：The synthesis of compound 4
By compound 3 (24.2g, 0.05mol), triethylamine (22.2g, 0.22mol), glycine methyl ester hydrochloride (7.5g,
Dichloromethane solution and HATU (20.9g, 0.055mol) mixing 0.06mol) is placed in 500mL three-necked bottle, and appropriate 4- is added
Dimethylamino naphthyridine is as catalyst, the reaction was continued at 35 DEG C 1h.Water is added into mixture, is extracted with dichloromethane, it is organic
Layer is washed with water 5-6 times, then dry with anhydrous magnesium sulfate.After suction filtration, filtrate removes solvent under reduced pressure.With silica gel column chromatography institute
Obtaining product, (eluant, eluent is petroleum ether：Ethyl acetate=1:2) the faint yellow viscous liquid, obtained is compound 4.
Embodiment 5：The synthesis of abietyl dipeptides surfactant R -11-2-Na
The ethyl alcohol and 0.4g water of NaOH (2g, 0.05mol), 80mL are added into the single port bottle of 250mL, stirs complete to NaOH
Fully dissolved adds compound 4 (27.7g, 0.05mol), reacts 3h at 70 DEG C.After completion of the reaction, solvent is removed under reduced pressure, obtains
To abietyl dipeptides surfactant R -11-2-Na.Yield：88%.
Wherein abietyl dipeptides surfactant R -11-2-Na1H NMR, as shown in Figure 1, it will be seen from figure 1 that should1H displacement in HNMR figure can be corresponded with target product, and without miscellaneous peak.Illustrate to have obtained target product abietyl two
Peptide surfactant R -11-2-Na, and purity meets follow-up test requirement.
Embodiment 6：The measurement of surface tension
The aqueous solution of the abietyl dipeptides surfactant R -11-2-Na of various concentrations a series of is prepared, experimental water is
The ultrapure water of resistivity 18.2M Ω cm, it is 12 that NaOH, which is added, and adjusts the pH value of solution.Configured surfactant is water-soluble
Liquid, which is placed in Air-Them air bath, to be balanced for 24 hours, and control equilibrium temperature is 25 ± 0.5 DEG C.Water is measured with hanging ring method at 25 DEG C
The surface tension of solution, each point are repeated 3 times, and take its average value, and the surface tension for drawing sample is bent with the variation relation of concentration
Line.
The surface tension γ of the abietyl dipeptides surfactant R -11-2-Na shown from Fig. 2 with concentration C change curve
Figure.
Figure it is seen that the surface tension value of the abietyl dipeptides surfactant R -11-2-Na is all reaching a certain
It is held essentially constant after concentration, this concentration is the critical micelle concentration of the surfactant.The critical glue of the surfactant
Beam concentration value is 0.23mmolL-1, illustrate that the surfactant can promote well surfactant molecule in aqueous solution
Aggregation forms micella, shows excellent ability of aggregation.γcmcFor 37.3mNm-1, C20Value is 0.09mmolL-1。
Embodiment 7：The measurement of rheological behaviour
The preparation of viscoelastic solution：The aqueous solution of R-11-2-Na is mixed with the aqueous solution of choline chloride (ChCl), the two is rubbed
You are than being 1:1.Obtain a series of aqueous solutions of R-11-2-Na/ChCl system.
By the aqueous solution of the R-11-2-Na/ChCl prepared a series of, constant temperature for 24 hours, uses model in 25 DEG C of insulating box
Viscoelastic properties test is carried out to the system for the rheometer of Discovery DHR-3.Stress Control mode is selected, cone-plate specification is
Standard ETC steel, cone angle are 1 °, and cone-plate diameter is 60mm.Before starting test, by sample pipetting volume to platform, trimming behaviour is carried out
After work, the sample solution of platform edges spilling is slowly scraped off, sample is then stood into balance 2min.Cone-plate peace when being tested
Final distance between platform is 29 μm.Sample first carries out strain sweep before testing, to determine the linear viscoelastic region of sample, it is ensured that institute
There is the test of sample to carry out in its linear viscoelastic region.At 25 DEG C, experimental water is 18.2M for temperature control in experimentation
The ultrapure water of Ω cm.
Fig. 3 shows viscosity of the viscoelastic solution R-11-2-Na/ChCl system under various concentration with the change of shear rate
Change.As can be seen from Figure 3 the viscosity of viscoelastic solution R-11-2-Na/ChCl system may be up to 1 × 103Pa·s.Surface-active
Agent concentration is more than 140mmolL-1Afterwards, when low shear rate, the viscosity of solution is basically unchanged with the increase of shear rate, performance
Typical Newtonian fluid behavior out；When high-rate of shear, the viscosity of solution reduces with the increase of shear rate, and it is dilute shearing occur
Change phenomenon, shows worm micella occur in R-11-2-Na/ChCl system at this time.
Fig. 4 shows elasticity modulus (G ') and sticky mould of the viscoelastic solution R-11-2-Na/ChCl system under various concentration
(G ") is measured with the variation of angular frequency (ω).Figure 4, it is seen that the dynamic viscoelasticity spectrum of all solution shows similar spy
Sign.In high frequency, elasticity modulus is higher than viscous modulus, and solution major embodiment goes out the elastic characteristic of itself；In low frequency, sticky mould
Amount is higher than elasticity modulus, and solution major embodiment goes out adhesive characteristics, shows that the solution has preferable viscoplasticity.
Claims (10)
1. a kind of abietyl dipeptides surfactant, which is characterized in that the structural formula of the abietyl dipeptides surfactant is such as
Under：
2. abietyl dipeptides surfactant according to claim 1, which is characterized in that abietyl dipeptides surface is living
Property agent is using the main component dehydroabietic acid in disproportionated rosin as Material synthesis.
3. abietyl dipeptides surfactant according to claim 1, which is characterized in that abietyl dipeptides surface is living
The synthetic route of property agent is as follows：
4. a kind of viscoelastic solution, which is characterized in that the viscoelastic solution is based on any abietyl two of claim 1-3
The viscoelastic solution of peptide surfactant.
5. viscoelastic solution according to claim 4, which is characterized in that the viscoelastic solution is that abietyl dipeptides surface is living
Property agent and choline chloride (ChCl) aqueous solution be mixed to get.
6. viscoelastic solution according to claim 5, which is characterized in that the abietyl dipeptides surfactant and chlorination gallbladder
The molar ratio of alkali is 1:1.
7. viscoelastic solution according to claim 5, which is characterized in that the viscoelastic solution, R-11-2-Na/ChCl system
In, the concentration range of abietyl dipeptides surfactant is 140-300mmolL-1。
8. viscoelastic solution according to claim 5, which is characterized in that the zero-shear viscosity of the viscoelastic solution up to 1 ×
103Pa·s。
Described in 9. claim 1-3 any the abietyl dipeptides surfactant or claim 4-8 is any
The application of viscoelastic solution.
10. application according to claim 9, which is characterized in that the application includes being used for personal care articles, oil field fracturing
Liquid, fluid drag-reduction agent.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2020140326A1 (en) * | 2019-01-04 | 2020-07-09 | 江南大学 | Rosin-based small molecule hydrogel agent and application thereof |
| CN115124438A (en) * | 2022-07-14 | 2022-09-30 | 江南大学 | Preparation and application of efficient natural product-based viscoelastic solution |
| CN116478677A (en) * | 2023-03-09 | 2023-07-25 | 陕西宏丰石油工程技术有限公司 | Self-steering shunt acidification method for reservoir of oil layer |
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Application publication date: 20181120 |