CN107879942A - A kind of bio-based primary amine cationic surfactant and preparation method thereof - Google Patents
A kind of bio-based primary amine cationic surfactant and preparation method thereof Download PDFInfo
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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Abstract
The invention discloses a kind of bio-based primary amine cationic surfactant and preparation method thereof, belong to surfactant science and applied technical field.The synthesis of the surfactant of the present invention is included being esterified, being reduced successively as initiation material using oleic acid and methanol, substitutes synthesis oleyl alcohol, and oleyl alcohol and 3 hydroxy benzaldehydes generation substitution, substitution, reduction, acidification reaction obtain final bio-based primary amine cationic surfactant.Raw material sources are wide, biorenewable, green, and biological degradability is high, enrich the species for the Bio-surfactant that renewable resource is raw material, can be widely used in the research of surfactant self-organizing system.
Description
Technical field
The present invention relates to a kind of bio-based primary amine cationic surfactant and preparation method thereof, belong to surfactant section
And applied technical field.
Background technology
Bio-surfactant is because its recyclability and excellent surface-active are increasingly by the extensive pass of people
Note.The present invention is to obtain a kind of new bio base primary amine cation surface activating by the reaction of seven steps using oleic acid as initiation material
Agent, and investigated its surface tension properties.
It is largely the derivative of nitrogenous organic matter, i.e. organic amine in cationic surfactant.The salt of simple amine
Sour (or other inorganic acids) salt and acetate etc., as PH ＞ 7, free amine easily separates out from the aqueous solution, so as to lose surface
Activity.
Cationic surfactant has excellent performance, and its performance and itself molecular configuration are closely related, with the moon from
Sub- surfactant is compared, and it can be used as emulsifying agent, dispersant, wetting agent, disinfectant, bactericidal agent in acidic aqueous solution,
Can mineral flotation agent, also act as pigment powder surface hydrophobicity agent.
Cationic surfactant is easily adsorbed at the surface of solids, surface is become hydrophobic；Then cation surface activating
Agent has some specific uses.Such as it is commonly used for mineral flotation agent, bitumen emulsion emulsifying agent, textile fabric softening agent and resists quiet
Electric agent, and pigment dispersing agent.Cationic surfactant also has a feature in addition to surface-active, i.e. its aqueous solution has
Very strong sterilizing ability.
Report on cationic surfactant is a lot, typically quaternary ammonium salt cationic surfactant.Primary amine sun
Ionic surface active agent is more difficult due to synthesizing, and research report is seldom.Due to primary amine cationic surfactant and quaternary ammonium sun
Difference on ion head based structures, the difference of intermolecular weak interaction power is result in, primary amine salt surfactant is compared to season
Ammonium surfactant has some special purposes, such as in terms of mineral floating, the Central South University relevant personnel work out primary
Amine cation surfactant is good to the FLOTATION SEPARATION effect of mica and quartz compared to quaternary surfactant.Such as Anhui
It is prominent compared to having in terms of quaternary surfactant wet coal preparation that Polytechnics works out primary amine salt ionic surface active agent
Effect.
But compared to quaternary surfactant for, the species of primary amine cationic surfactant is not abundant enough, grinds
The extensiveness and intensiveness studied carefully is limited, and it is of a relatively high to synthesize cost.Liu Gousheng seminars of East China University of Science once utilize stearic acid
Primary amine ionic surface active agent of the synthesis with 12 carbon chain lengths, the cmc of its ten di-primary amines surfactant is 12mmol/
L。
The content of the invention
The present invention is reduction critical micelle concentration, strengthens the ability of aggregation of primary amine ionic surface active agent, wide using source
It is general, there is the oleic acid of 18 chain lengths as raw material, and phenyl ring is introduced in hydrophobic tail chain, its molecule is obtained in interface arrangement
More closely strengthen its water delivery and ability of aggregation, it is synthesized go out the cmc of oleic acid base primary amine cationic surfactant be
0.251mmol/L。
First purpose of the present invention is to provide a kind of bio-based primary amine cationic surfactant, and structural formula is as follows：
In one embodiment of the invention, the anion portion of the bio-based primary amine cationic surfactant is
Cl- or Br-.
Second object of the present invention is to provide the preparation method of the bio-based primary amine cationic surfactant, described
Method is to be esterified, reduced successively as initiation material using oleic acid and methanol, substituting synthesis oleyl alcohol, oleyl alcohol and 3- hydroxy benzaldehydes
Generation substitution, substitution, reduction, acidification reaction obtain final bio-based primary amine cationic surfactant.
In one embodiment of the invention, the preparation method is specially：Using oleic acid and methanol as starting ester metaplasia
Into methyl oleate, methyl oleate reduction generation oleyl alcohol, oleyl alcohol and the thionyl chloride reaction generation chloro- cis -9- octadecylenes of 1-, 1-
Chloro- cis -9- octadecylenes and 3- hydroxy benzaldehydes reaction generation (E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehyde, (E) -
3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehydes and azanol hydrochloric acid reaction generation 3- (Linolenic Acid-alkene -1- bases epoxide) benzene first
Aldoxime, 3- (Linolenic Acid-alkene -1- bases epoxide) benzaldoximes and lithium aluminium hydride reduction reaction generation (E)-(3- (Linolenic Acids-alkene -1-
Base epoxide) phenyl) methylamine, (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methylamine and hcl reaction generation (E) -
(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) ammonio methacrylate.
In one embodiment of the invention, the mol ratio of the oleic acid and methanol is 1:2~2:1.
In one embodiment of the invention, the reaction of the oleic acid and methanol, is under conditions of containing the concentrated sulfuric acid
Carry out.
In one embodiment of the invention, the reaction condition of the oleic acid and methanol is 70 DEG C~75 DEG C reaction 4-5
Hour.
In one embodiment of the invention, the methyl oleate reduction reaction, it is in the condition containing lithium aluminium hydride reduction
Lower progress.
In one embodiment of the invention, the methyl oleate reduction reaction conditionses are 30 DEG C~35 DEG C reaction 3-4
Hour
In one embodiment of the invention, the mol ratio of the reaction of the oleyl alcohol and thionyl chloride is 1:2~2:1.
In one embodiment of the invention, the reaction of the oleyl alcohol and thionyl chloride, it is in the condition containing pyridine
Lower progress.
In one embodiment of the invention, the reaction condition of the oleyl alcohol and thionyl chloride is 70 DEG C~75 DEG C reactions
4-5 hours.
In one embodiment of the invention, the mol ratio of the chloro- cis -9- octadecylenes of the 1- and 3- hydroxy benzaldehydes
For 1:2~2:1.
In one embodiment of the invention, the reaction of the chloro- cis -9- octadecylenes of the 1- and 3- hydroxy benzaldehydes,
It is to be carried out in the DMF mixed solutions containing KI.
In one embodiment of the invention, the reaction bar of the chloro- cis -9- octadecylenes of the 1- and 3- hydroxy benzaldehydes
Part is 110 DEG C~120 DEG C reaction 24-36h.
In one embodiment of the invention, described (E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehydes and azanol
The mol ratio of the reaction of hydrochloric acid is 1:2~2:1.
In one embodiment of the invention, (E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehydes and azanol hydrochloric acid
Reaction, be to be carried out under the conditions of the ethanol solution containing pyridine.
In one embodiment of the invention, (E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehydes and azanol hydrochloric acid
Reaction condition be 70 DEG C~80 DEG C reaction 1-2 hours.
In one embodiment of the invention, 3- (Linolenic Acid-alkene -1- bases epoxide) benzaldoximes and lithium aluminium hydride reduction
Reduction reaction, carried out under the conditions of the tetrahydrofuran solution containing lithium aluminium hydride reduction.
In one embodiment of the invention, 3- (Linolenic Acid-alkene -1- bases epoxide) the benzaldoxime reduction reaction
Condition is 30 DEG C~35 DEG C reaction 1-2 hours
In one embodiment of the invention, (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methylamine and chlorination
The mol ratio of the reaction of hydrogen is 1:2~2:1.
In one embodiment of the invention, (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methylamine and chlorination
The reaction of hydrogen, carried out under conditions of concentrated sulfuric acid drying.
In one embodiment of the invention, the specific reaction equation of the preparation method is as follows：
(E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) synthetic route of ammonio methacrylate：
Third object of the present invention is to provide the viscoelastic system that the bio-based primary amine cationic surfactant is constructed.
Fourth object of the present invention is to provide the biology that the bio-based primary amine cationic surfactant is prepared
Film.
The 5th purpose of the present invention is to provide the application of described bio-based primary amine cationic surfactant.
In one embodiment of the invention, the application be applied to environmental area, field of textiles, chemical field,
Prepare drug field, industry cleaning link, household chemicals.
In one embodiment of the invention, the application includes：Applied to environmental protection, oilfield exploitation, weaving print
Dye, industry cleaning link, household chemicals.
Beneficial effects of the present invention：
(1) new bio base primary amine cationic surfactant of the invention contains that raw material sources are wide, and biorenewable is green
Colour circle is protected, and biological degradability is high, enriches the species for the Bio-surfactant that renewable resource is raw material, can extensive use
In the research of surfactant self-organizing system.By the use of the oleic acid with 18 chain lengths as raw material, and in hydrophobic tail
Phenyl ring is introduced in chain, its molecule is obtained more close its water delivery of enhancing and ability of aggregation in interface arrangement.If from short carbon chain
Saturated fatty acid does not have overlength chain oleic acid as raw material as initiation material, the self assembly ability and aggregation pattern of surfactant
The surfactant of formation is rich and varied.Oleic acid base primary amine cationic surfactant can produce vesica generation at low concentrations
Bilayer vesicle, expand the direction of biomembrane research.Bio-based primary amine cationic surfactant (E)-(3- (ten of the present invention
Eight carbon -9- alkene -1- bases epoxides) phenyl) ammonio methacrylate critical micelle concentration it is relatively low, cmc 0.251mmol/L, critical
The surface tension γ cmc of surfactant under micellar concentration are 28.8mNm.
(2) present invention reacts synthesizing new bio-based primary amine cationic surfactant through seven steps, visited using oleic acid as raw material
The actual conditions of rope reaction.By rationally controlling reaction time and reaction condition, be advantageous to improve reaction yield, reduce final
The difficulty of purifying products.
(3) bio-based primary amine cationic surfactant of the invention can be widely applied to mineral flotation agent, pitch breast
Shape liquid emulsifying agent, textile fabric softening agent and antistatic additive, and the numerous areas such as pigment dispersing agent.
(4) present invention carries out extracting operation using the petroleum ether of nontoxic low polarity, improves experiment safety.The present invention uses
Oximido is successfully reverted to benzamido group by this new reducing agent being easy to get of lithium aluminium hydride reduction, and yield has been lifted.
Brief description of the drawings
Fig. 1 is the nuclear magnetic resonance 1HNMR spectrograms of bio-based primary amine cationic surfactant；
Fig. 2 is surface tension curve of the bio-based primary amine cationic surfactant at 25 DEG C；
Fig. 3 is aggregate size data of the bio-based primary amine cationic surfactant under various concentrations.
Embodiment
Embodiment 1：Bio-based primary amine cationic surfactant synthetic route
Bio-based primary amine cationic surfactant, structural formula are as follows：
The synthetic route of bio-based primary amine cationic surfactant is as follows：
The preparation method of new bio base primary amine cationic surfactant, it is characterised in that methods described is first with oil
Acid and methanol are that initiation material is esterified, reduced, substitute synthesis oleyl alcohol successively, oleyl alcohol and 3- hydroxy benzaldehydes occur to substitute,
Substitution, reduction, acidification reaction obtain final bio-based primary amine cationic surfactant.
Embodiment 2：The synthesis of methyl oleate
By the centrifugal bottle equipped with oleic acid, white solid precipitation, after solid is filtered out, liquid are arranged at low-temperature centrifugation, bottom at 5 DEG C
Body can be used for subsequent reactions.By oleic acid (200g 0.71mol), absolute methanol (160g 5mol) and the concentrated sulfuric acid (3g) are added to
In 500ml single port bottles, reacted 4 hours at 72 DEG C, after reaction terminates, revolving removes methanol.Then organic layer is washed with water, finally
Organic layer is dried with magnesium sulfate, methyl oleate sterling is obtained by filtering, being evaporated under reduced pressure.172 DEG C~175 DEG C/5mmHg.Yield
71%.
Embodiment 3：The synthesis of oleyl alcohol
Lithium aluminium hydride reduction (12g, 0.316mol), tetrahydrofuran 220ml are put into 500ml single port bottles, are then put into ethanol
In ice bath, then methyl oleate (90g, 0.3mol) is slowly added into reaction system with constant pressure separatory funnel, after adding-
Stirred half an hour at 10 DEG C, then system temperature is raised to 30 DEG C and reacted 3 hours, reactant is cooled to -10 DEG C, adds 12g
Water, 12g dilute solution of sodium hydroxide, 40g anhydrous sodium sulfates.Filtered after being sufficiently mixed, then filtrate is rotated and removes solvent, both
Oleyl alcohol.Yield 80%.
Embodiment 4：Chloro- cis -9- octadecylenes the synthesis of 1-
Oleyl alcohol (60g, 0.22mol), pyridine (40g, 0.51mol) are added in three-neck flask, at the same reflux condensation mode with
Tail gas recycle.Then thionyl chloride is slowly dropped at 30 DEG C, after being added dropwise, be sufficiently stirred temperature is slow after half an hour
Rise to 70 DEG C to continue after reacting 4 hours, temperature of reaction system is turned off, slow cooling.Then reactant mixture is placed in 500ml
Half an hour is rotated in single-necked flask, suitable quantity of water is added thereto and reacts away the thionyl chloride of excess, then add 100ml stones
Oily ether extraction.Oil reservoir is successively washed till neutrality with dilute acetic acid solution, dilute sodium carbonate solution.It is dried overnight, is revolved with anhydrous magnesium sulfate
Petroleum ether is evaporated off, the chloro- cis -9- octadecylenes sterlings of 1- for being finally evaporated under reduced pressure reactant mixture.192 DEG C~195 DEG C/
5mmHg.Yield 85%.
Embodiment 5：(E) synthesis of -3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehyde
By 3- hydroxy benzaldehydes (20g, 0.16mol), Anhydrous potassium carbonate (68.4g, 0.48mol), KI (33.2g,
0.20mol) and 200mlN, dinethylformamide are added to the 500ml tri- with condensation reflux unit and device for recovering tail gas
In neck flask, while nitrogen is protected.Then 40 DEG C are risen to, the chloro- cis -9- octadecylenes (49.2g, 0.18mol) of 1- are used into constant pressure
Separatory funnel is slowly added into reaction system, and reaction temperature is risen into 100 DEG C after being added dropwise, and continues reaction 24 hours.Instead
DMF is rotated after should terminating and removed, 150ml petroleum ethers is added, is then washed with 15% sodium chloride weak solution
Organic layer.It is dried overnight with anhydrous magnesium sulfate, revolving removes petroleum ether, both obtains (E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzene
Formaldehyde.Yield 75%.
Embodiment 6：The synthesis of 3- (Linolenic Acid-alkene -1- bases epoxide) benzaldoxime
Hydroxylamine hydrochloride (18.46g, 0.266mol), pyridine (20ml) and ethanol (150ml) are placed in be filled with condensing reflux
Put in the 500ml three-neck flasks with device for recovering tail gas, while nitrogen is protected.40 degree are warming up to, and will with constant pressure separatory funnel
(E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehyde (44g, 0.12mol) is slowly added to.After addition, temperature is risen to
75 DEG C, continue reaction 1 hour.Reaction system is down to room temperature, revolving removes ethanol, adds 150ml petroleum ethers, is washed with water organic
Three times removing excess pyridine of layer.It is dried overnight with anhydrous magnesium sulfate, revolving removes petroleum ether.Finally recrystallized with ethanol (95%)
Both 3- (Linolenic Acid-alkene -1- bases epoxide) benzaldoxime sterling is obtained.Yield 71%.
Embodiment 7：(E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) synthesis of methylamine
Lithium aluminium hydride reduction (4.85g, 0.13mol), tetrahydrofuran 150ml are put into 500ml single port bottles, are then put into ethanol
In ice bath, then 3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehyde (32g, 0.085mol) is slowly added with constant pressure separatory funnel
Enter into reaction system, stirred half an hour at -10 DEG C after adding, then system temperature is raised to 30 DEG C and reacted 1 hour, will be anti-
Answer thing to cool to -10 DEG C, add 100g water.Revolving removes tetrahydrofuran, filters and separates liquid phase with solid phase, by liquid phase ether
Extraction, is dried overnight with anhydrous magnesium sulfate, and revolving removes ether, both obtains (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl)
Methylamine.Yield 78%.
Embodiment 8：(E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) synthesis of ammonio methacrylate
(E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methylamine (23.47g, 0.065mol) is dissolved in 100ml second
It is placed among ether in 500ml three-necked flask, is passed through dry HCl gases and is allowed into salt, obtain white solid, with dichloromethane weight
Crystallization three times, produces (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) ammonio methacrylate (21.3g, 0.052mol).Production
Rate 80%.
Embodiment 9：(E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) nuclear magnetic resonance of ammonio methacrylate1HNMR is composed
And property
The end-product nuclear magnetic resonance 1HNMR spectrums that embodiment 8 obtains are shown in Fig. 1.
According to Fig. 1 nuclear magnetic resoance spectrum map analysis, final product (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) first
Ammonium chloride is dissolved with CD3Cl, measures 1HNMR spectrums.It is CD3Cl solvent peak at δ=7.26 in Fig. 1.Remaining proton displacement δ
For：8.52(m,3H),7.35-6.75(t,4H),5.35(t,3H),4.00-3.75(t,4H),2.25-1.25(q,28H),
0.88(t,3H).From the data cases analysis of spectrogram processing, it can learn that final product is consistent with design object product.
Bio-based primary amine cationic surfactant (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methyl chloride
The measure of ammonium surface tension, the surface tension of the reaction mixture of various concentrations is measured using surface tension method, makees 25 DEG C
Under (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methyl chloride aqueous ammonium surface tension with solution concentration change
Curve, see Fig. 2.
Concentration corresponding to curve break is the critical micelle concentration cmc of the surfactant in Fig. 2, the curve from figure
Ordinate corresponding to turning point can obtain the surface tension γ cmc of the surfactant.Experiment find, bio-based primary amine sun from
The critical micelle concentration of sub- surfactant (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) ammonio methacrylate is relatively low,
Cmc is 0.251mmol/L, and the surface tension γ cmc of the surfactant under critical micelle concentration are 28.8mNm.East China
Liu Gousheng seminars of Polytechnics once had the primary amine ionic surface active agent of 12 carbon chain lengths using stearic acid synthesis, its
The cmc of ten di-primary amine surfactants is 12mmol/L, there is the quaternary ammonium that document report is synthesized by 18 carbon saturated fatty acids in addition
The γ cmc of salt surfactant are 38.5mNm.Ability of aggregation of the invention by strengthening primary amine ionic surface active agent, profit
By the use of the oleic acid with 18 chain lengths as raw material, and phenyl ring is introduced in hydrophobic tail chain, its molecule is obtained in interface arrangement
More closely strengthen its water delivery and ability of aggregation, effectively reduce CMC and γ cmc.
Bio-based primary amine cationic surfactant (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methyl chloride
Ammonium can produce vesica and produce bilayer vesicle at low concentrations, as a result as shown in figure 3, can see vesicle size from figure with molten
Liquid concentration becomes big and diminished, and meets the universal law of vesica change.
Although the present invention is disclosed as above with preferred embodiment, it is not limited to the present invention, any to be familiar with this skill
The people of art, without departing from the spirit and scope of the present invention, it can all do various change and modification, therefore the protection model of the present invention
Enclose being defined of being defined by claims.
Claims (10)
- A kind of 1. bio-based primary amine cationic surfactant, it is characterised in that the knot of the primary amine cationic surfactant Structure formula is as follows：
- 2. primary amine cationic surfactant according to claim 1, it is characterised in that the primary amine cationic surface is lived The anion portion of property agent is Cl- or Br-.
- 3. the preparation method of the bio-based primary amine cationic surfactant described in a kind of claim 1, it is characterised in that described Method is first to be esterified, reduced successively as initiation material using oleic acid and methanol, substituting synthesis oleyl alcohol, oleyl alcohol and 3- hydroxy benzenes first Aldehyde generation substitution, substitution, reduction, acidification reaction obtain final bio-based primary amine cationic surfactant.
- 4. according to the method for claim 3, it is characterised in that methods described concretely comprises the following steps：Using oleic acid and methanol as original Material esterification generation methyl oleate, methyl oleate reduction generation oleyl alcohol, oleyl alcohol and the chloro- cis -9- ten of thionyl chloride reaction generation 1- Eight alkene, the chloro- cis -9- octadecylenes of 1- and 3- hydroxy benzaldehydes reaction generation (E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzene first Aldehyde, (E) -3- (Linolenic Acid-alkene -1- bases epoxide) benzaldehydes and azanol hydrochloric acid reaction generation 3- (Linolenic Acids-alkene -1- base oxygen Base) benzaldoxime, 3- (Linolenic Acid-alkene -1- bases epoxide) benzaldoximes and lithium aluminium hydride reduction reaction generation (E)-(3- (18 carbon - 9- alkene -1- bases epoxide) phenyl) methylamine, (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) methylamine and hcl reaction life Into (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) ammonio methacrylate.
- 5. according to the method for claim 4, it is characterised in that the specific reaction equation of the preparation method is as follows：The synthetic route of product (E)-(3- (Linolenic Acid-alkene -1- bases epoxide) phenyl) ammonio methacrylate：
- 6. according to the method for claim 4, it is characterised in that methods described is to be used as extractant using petroleum ether.
- 7. the viscoelastic system that any described bio-based primary amine cationic surfactant of claim 1~2 is constructed.
- 8. the biomembrane that any described bio-based primary amine cationic surfactant of claim 1~2 is prepared.
- 9. the application of any described bio-based primary amine cationic surfactant of claim 1~2.
- 10. application according to claim 8, it is characterised in that the application be applied to environmental area, field of textiles, Chemical field, prepare drug field, industry cleaning link, household chemicals.
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| CN106279089A (en) * | 2015-06-11 | 2017-01-04 | 南京华迈生物医药科技有限公司 | Formoononetin aliphatic ether analog derivative, its preparation method and medical usage |
-
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279089A (en) * | 2015-06-11 | 2017-01-04 | 南京华迈生物医药科技有限公司 | Formoononetin aliphatic ether analog derivative, its preparation method and medical usage |
Non-Patent Citations (3)
| Title |
|---|
| 宋冰蕾等: "油酸基三聚表面活性剂的合成与性能", 《化工进展》 * |
| 韩莹等: "４－十二烷氧基苄胺在纳米金微粒合成中的应用", 《化学研究》 * |
| 韩莹等: "新型双链表面活性剂DDOBA的合成与高单分散性憎水纳米金的制备", 《物理化学学报》 * |
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