CN105879772A - Trimeric anionic surfactant with long rigid linking group and viscoelastic solution formed by trimeric anionic surfactant - Google Patents

Trimeric anionic surfactant with long rigid linking group and viscoelastic solution formed by trimeric anionic surfactant Download PDF

Info

Publication number
CN105879772A
CN105879772A CN201610292622.5A CN201610292622A CN105879772A CN 105879772 A CN105879772 A CN 105879772A CN 201610292622 A CN201610292622 A CN 201610292622A CN 105879772 A CN105879772 A CN 105879772A
Authority
CN
China
Prior art keywords
anionic surfactant
trimeric
solution
surfactant
viscoelastic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201610292622.5A
Other languages
Chinese (zh)
Other versions
CN105879772B (en
Inventor
宋冰蕾
周萍萍
翟兆兰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiuer Xi'an Intellectual Property Service Co ltd
Shandong Daming Fine Chemical Co ltd
Original Assignee
Jiangnan University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangnan University filed Critical Jiangnan University
Priority to CN201610292622.5A priority Critical patent/CN105879772B/en
Publication of CN105879772A publication Critical patent/CN105879772A/en
Application granted granted Critical
Publication of CN105879772B publication Critical patent/CN105879772B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • 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
    • C09K8/66—Compositions based on water or polar solvents
    • C09K8/68—Compositions based on water or polar solvents containing organic compounds
    • 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
    • C09K8/84—Compositions based on water or polar solvents
    • C09K8/86—Compositions based on water or polar solvents containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/06—Ether- or thioether carboxylic acids
    • 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
    • C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
    • C09K2208/30—Viscoelastic surfactants [VES]

Abstract

The invention relates to a trimeric anionic surfactant with a long rigid linking group and a viscoelastic solution formed by the trimeric anionic surfactant, wherein the molecular structure of the trimeric anionic surfactant C-TrisPhC<n>Na(n=10,12,14) is show as the accompanying drawing, and R=C<n>H2<n+1>(n=10,12,14); the trimeric anionic surfactant can form the viscoelastic solution under the condition without any additives. When the hydrophobic chain length of the C-TrisPhC<n>Na is greater, the viscoelastic performance of the formed solution is better. When the concentration of the surfactant is only 65mmol L<-1>, the zero shear viscosity of a C-TrisPhC14Na solution can reach 1380Pa s. As a one-class anionic surfactant, the C-TrisPhC<n>Na has good biocompatibility; the formed viscoelastic solution can be applied to formulas of oil field fracturing fluid, dragging drag reducers and daily detergents.

Description

One class has the trimerization anion surface active agent of long rigid attachment base and formation thereof Viscoelastic solution
Technical field
The present invention relates to the viscoelastic solution of a class trimerization anion surface active agent and formation thereof, contain particularly to one The trimerization anion surface active agent of long rigid attachment base and the viscoelastic solution of formation thereof, belong to surfactant scientific domain.
Background technology
Surfactant viscoelastic solution has a wide range of applications in daily life and commercial production, as oil field is adopted The fracturing fluid used in oil, pulls drag reducer and daily cleaning agent prescription etc..Common surfactant viscoelastic solution system can It is divided into surfactant/salt system or mixed surfactant system.But, this kind of system typically requires higher surface activity Agent concentration, this makes the application cost of surfactant viscoelastic solution higher.Simultaneously as this kind of viscoelastic solution is by various ingredients Compounding formation, when using (such as rock stratum or soil) in some has the system of complicated interface, can produce chromatographic fractionation effect, make Obtain mixed solution and lose viscoelasticity, reduce its application performance.On the other hand, also system can be caused unnecessary pollution, increase Add the difficulty of post processing.
The viscoelasticity of surfactant solution is closely related with the molecular structure of surfactant.Oligo surfactant contains There is different kinds of molecules structural element, asymmetric aggregated structure such as rod-shaped micelle or anthelmintic glue can be self-assembly of under low concentration Bundles etc., make solutions display go out the strongest viscoelasticity, cause the broad interest of people in recent years.Oligomeric surface is lived by spacer group The self-organizing behavioral implications of property agent is notable.If suitable spacer group, the molecule of appropriate design oligo surfactant can be selected Structure, then be expected to the effect not against any additive, it is thus achieved that has high viscoelastic surfactant solution system.
Summary of the invention
For the defect overcoming current surfactant viscoelastic solution to exist in application aspect, the present invention utilizes 1, and 1,1-tri- The molecular characterization of (4-hydroxyphenyl) ethane, as the long rigid attachment group of terpolymer surfactant, has synthesized one Class can form the trimerization anion surface active agent of viscoelastic solution without any additive.
The technical scheme is that with 1,1,1-tri-(4-hydroxyphenyl) ethane is spacer group, synthesizes a class trimerization cloudy Ionic surface active agent C-TrisPhCnNa (n is the carbon number contained by surfactant hydrophobic alkane chain).Again by this surface Activating agent is dissolved in water, forms viscoelastic solution.Wherein trimerization anion surface active agent C-TrisPhCnThe structural formula of Na is as follows:
Trimerization anion surface active agent C-TrisPhCnThe synthetic route of Na (n=10,12,14) is as follows:
By a certain amount of trimerization anion surface active agent C-TrisPhCnNa (n=10,12,14) is dissolved in water, can obtain Obtain corresponding surfactant viscoelastic solution.
Beneficial effect
Containing the trimerization anion surface active agent of long rigid attachment base, in the case of not against any additive Formation has good viscoelastic solution.The defects such as use cost, the chromatographic fractionation effect in elimination use can be reduced.Can apply In oil field fracturing fluid, the formula of towing drag reducer or daily cleaning agent.
Accompanying drawing explanation
Fig. 1 C-TrisPhC10The nuclear magnetic spectrogram (recording in MeOD) of Na.
Fig. 2 C-TrisPhC12The nuclear magnetic spectrogram (recording in MeOD) of Na.
Fig. 3 C-TrisPhC14The nuclear magnetic spectrogram (recording in MeOD) of Na.
C-TrisPhC under Fig. 4 variable concentrations10The viscosity of Na solution is with the change curve of shear rate.
C-TrisPhC under Fig. 5 variable concentrations12The viscosity of Na solution is with the change curve of shear rate.
C-TrisPhC under Fig. 6 variable concentrations14The viscosity of Na solution is with the change curve of shear rate.
Fig. 7 trimerization anion surface active agent (C-TrisPhCnNa, n=10,12,14) zero-shear viscosity of solution is with dense The change curve of degree.
Detailed description of the invention
Embodiment 1: the synthesis of alpha-brominated methyl dodecanoate.Lauric acid/dodecanoic acid (68.8g, 0.4mol) is added 500mL there-necked flask In, melt at 65 DEG C, be slowly added dropwise thionyl chloride (67.6g, 0.56mol) under stirring, drip and temperature is increased to 90 DEG C, Add a little elemental iodine as initiator, be slowly added dropwise through the dried bromine (73.6g, 0.46mol) of concentrated sulphuric acid, be stirred at reflux 12 hours, cool the temperature to 65 DEG C, the lower dropping absolute methanol 60mL of stirring, refluxes 2-4 hour after adding.3-is washed with water after cooling 4 times, then with saturated sodium bisulfite solution 50mL washing organic layer to neutral, be finally washed with water 3-4 time.Organic layer adds anhydrous Magnesium sulfate is dried overnight.After filtration, alpha-brominated methyl dodecanoate is distilled to obtain in crude product decompression.154～158 DEG C/5mmHg.
Embodiment 2: the synthesis of alpha-brominated methyl myristate.Tetradecylic acid (150g, 0.6568mol) is added 500mL tri-mouthfuls In Ping, melt at 65 DEG C, be slowly added dropwise thionyl chloride (106.6g, 0.821mol) under stirring, drip and temperature is increased to 90 DEG C, add a little elemental iodine as initiator, be slowly added dropwise through the dried bromine (131.2g, 0.821mol) of concentrated sulphuric acid, It is stirred at reflux 12 hours, cools the temperature to 65 DEG C, the lower dropping absolute methanol 120mL of stirring, refluxes 2-4 hour after adding.Cooling After wash with water 3-4 time, then with saturated sodium bisulfite solution 50mL washing organic layer to neutral, be finally washed with water 3-4 time.Organic Layer adds anhydrous magnesium sulfate and is dried overnight.After filtration, alpha-brominated methyl myristate is distilled to obtain in crude product decompression.175～180 DEG C/ 5mmHg。
Embodiment 3: the synthesis of alpha-brominated methyl palmitate.Hexadecylic acid (150g, 0.58mol) is added 500mL there-necked flask In, melt at 65 DEG C, be slowly added dropwise thionyl chloride (95.1g, 0.73mol) under stirring, drip and temperature is increased to 90 DEG C, Add a little elemental iodine as initiator, be slowly added dropwise through the dried bromine (116.6g, 0.73mol) of concentrated sulphuric acid, stir back Flow 12 hours, cool the temperature to 65 DEG C, the lower dropping absolute methanol 80mL of stirring, refluxes 2-4 hour after adding.Wash with water after cooling 3-4 time, then with saturated sodium bisulfite solution 50mL washing organic layer to neutral, be finally washed with water 3-4 time.Organic layer adds nothing Water magnesium sulfate is dried overnight.After filtration, alpha-brominated methyl palmitate is distilled to obtain in crude product decompression.192～196 DEG C/5mmHg.
Embodiment 4:C-TrisPhC10The synthesis of Na.By 1,1,1-tri-(4-hydroxyphenyl) ethane (8.1g, 0.026mol), warp The DMF (100mL) that molecular sieve after activation processed adds in the three-necked bottle of 500mL, and nitrogen atmosphere prevents Phenolic hydroxyl group aoxidizes.Add Anhydrous potassium carbonate (28g, 0.207mol), be warming up to 60 DEG C, the alpha-brominated methyl dodecanoate of disposable addition (31.2g, 0.104mol) (is dissolved in the DMF of 40mL), is warming up to 85 DEG C after 2h, reacts 24 hours.Cold But after, sucking filtration obtains yellow filtrate, by the DMF removed under reduced pressure in filtrate.Filtrate is transferred in separatory funnel, First add 60mL petroleum ether, add 80mL frozen water washing organic layer 3-4 time.Organic layer is separated, adds anhydrous magnesium sulfate and be dried, Removed under reduced pressure petroleum ether after filtration.Residue uses column chromatography, and eluant starts with petroleum ether, later with petroleum ether and acetic acid The mixed liquor (volume ratio is 10:1) of ethyl ester.Obtain light yellow viscous liquid.Productivity is 70.8%.By this liquid (13g, 0.014mol), sodium hydroxide (1.9g, 0.046mol) and 100mL dehydrated alcohol are equipped with the single port flask of reflux condensing tube In.Temperature is raised to 85 DEG C of backflows overnight.Reactant mixture is centrifuged to obtain white precipitate.Precipitation uses absolute ethanol washing four times, End product C-TrisPhC it is dried to obtain in vacuum drying oven10Na.Productivity is 75.6%.
Embodiment 5:C-TrisPhC12The synthesis of Na.By 1,1,1-tri-(4-hydroxyphenyl) ethane (8.5g, 0.028mol), warp The DMF (100mL) that molecular sieve after activation processed adds in the three-necked bottle of 500mL, and nitrogen atmosphere prevents Phenolic hydroxyl group aoxidizes.Add Anhydrous potassium carbonate (28g, 0.207mol), be warming up to 60 DEG C, the alpha-brominated methyl myristate of disposable addition (17.8g, 0.056mol) (is dissolved in the DMF of 45mL), is warming up to 85 DEG C after 2h, reacts 24 hours.Cold But after, sucking filtration obtains yellow filtrate, by the DMF removed under reduced pressure in filtrate.Filtrate is transferred in separatory funnel, First add 60mL petroleum ether, add 80mL frozen water washing organic layer 3-4 time.Organic layer is separated, adds anhydrous magnesium sulfate and be dried, Removed under reduced pressure petroleum ether after filtration.Residue uses column chromatography, and eluant starts with petroleum ether, later with petroleum ether and acetic acid The mixed liquor (volume ratio is 10:1) of ethyl ester.Obtain light yellow viscous liquid.Productivity is 75.4%.By this liquid (23g, 0.022mol), sodium hydroxide (2.95g, 0.074mol) and 100mL dehydrated alcohol are equipped with the single port flask of reflux condensing tube In.Temperature is raised to 85 DEG C of backflows overnight.Reactant mixture is centrifuged to obtain white precipitate.Precipitation uses absolute ethanol washing four times, End product C-TrisPhC it is dried to obtain in vacuum drying oven12Na.Productivity is 77.9%.
Embodiment 6:C-TrisPhC14The synthesis of Na.By 1,1,1-tri-(4-hydroxyphenyl) ethane (8.4g, 0.027mol), warp The DMF (100mL) that molecular sieve after activation processed adds in the three-necked bottle of 500mL, and nitrogen atmosphere prevents Phenol aoxidizes.Add Anhydrous potassium carbonate (28g, 0.207mol), be warming up to 60 DEG C, the alpha-brominated methyl palmitate of disposable addition (38.3g, 0.100mol) (is dissolved in the DMF of 60mL), is warming up to 85 DEG C after 2h, reacts 24 hours.Cold But after, sucking filtration obtains yellow filtrate, by the DMF removed under reduced pressure in filtrate.Filtrate is transferred in separatory funnel, First add 60mL petroleum ether, add 80mL frozen water washing organic layer 3-4 time.Organic layer is separated, adds anhydrous magnesium sulfate and be dried, Removed under reduced pressure petroleum ether after filtration.Residue uses column chromatography, and eluant starts with petroleum ether, later with petroleum ether and acetic acid The mixed liquor (volume ratio is 10:1) of ethyl ester.Obtain light yellow viscous liquid.Productivity is 71.7%.By this liquid (25.9g, 0.023mol), sodium hydroxide (3.075g, 0.077mol) and 100mL dehydrated alcohol are equipped with the single port burning of reflux condensing tube In Ping.Temperature is raised to 85 DEG C of backflows overnight.Reactant mixture is centrifuged to obtain white precipitate.Precipitation absolute ethanol washing four Secondary, dried end product C-TrisPhC in vacuum drying oven14Na.Productivity is 80.6%.
Embodiment 7: the preparation of surfactant solution.Weigh a certain amount of C-TrisPhC respectively10Na、C- TrisPhC12Na and C-TrisPhC14Na solid, is dissolved in the water of certain volume, i.e. obtains series of surfactants solution.
Embodiment 8: trimerization anion surface active agent C-TrisPhCnThe viscoelasticity of Na (n=10,12,14) solution is surveyed Amount.Series of surfactants solution is stood at 25 DEG C 48h, and at 25 DEG C, carries out the test of stable state rheological property.Result As shown in Figure 4, Figure 5 and Figure 6.After exceeding finite concentration, surfactant solution shows shear thinning phenomenon, illustrates to have bright Aobvious viscoelasticity.Fig. 7 is the zero-shear viscosity (η of three individual system0) with the change of concentration.Hydrophobic tail chain is the longest, zero-shear viscosity Increase with concentration is the rapidest.C-TrisPhC12Na and C-TrisPhC14Na solution occurs maximum on curve, this be due to In solution, the change of micro structure is caused.

Claims (4)

1. a class has the trimerization anion surface active agent of long rigid attachment base, and its molecular structure is as follows:
2. the trimerization anion surface active agent with long rigid attachment base described in a class claim 1, it is characterised in that be Reaction obtains as the following formula:
。
3. a class surfactant viscoelastic solution, is trimerization the moon that the class described in claim 1 has long rigid attachment base Ionic surface active agent is dissolved in water and obtains.It is characterized in that, as surfactant hydrophobic tail chain institute carbon atom quantity n=10, The concentration range forming viscoelastic solution is 100-250mmol L-1；As surfactant hydrophobic tail chain institute carbon atom quantity n=12 Time, the concentration range forming viscoelastic solution is 60-200mmol L-1；As surfactant hydrophobic tail chain institute carbon atom quantity n= When 14, the concentration range forming viscoelastic solution is 40-100mmol L-1。
4. the surfactant viscoelastic solution described in a class claim 3, it is characterised in that such surfactant forms viscoelastic Any additive is need not during solution.
CN201610292622.5A 2016-05-04 2016-05-04 One class has the trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation Active CN105879772B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610292622.5A CN105879772B (en) 2016-05-04 2016-05-04 One class has the trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610292622.5A CN105879772B (en) 2016-05-04 2016-05-04 One class has the trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation

Publications (2)

Publication Number Publication Date
CN105879772A true CN105879772A (en) 2016-08-24
CN105879772B CN105879772B (en) 2017-10-10

Family

ID=56702229

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610292622.5A Active CN105879772B (en) 2016-05-04 2016-05-04 One class has the trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation

Country Status (1)

Country Link
CN (1) CN105879772B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106588708A (en) * 2016-11-18 2017-04-26 塔里木大学 Method for synthesizing Gemini surfactant
CN108837773A (en) * 2018-06-20 2018-11-20 江南大学 A kind of viscoelastic solution formed by abietyl dipeptides surfactant

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102167673A (en) * 2011-03-14 2011-08-31 广东工业大学 Surfactant containing adamantane and preparation method thereof
CN102899901A (en) * 2012-10-23 2013-01-30 金发科技股份有限公司 High-temperature-resistant emulsion type carbon fiber sizing agent and preparation and applications of carbon fiber sizing agent
JP2014129302A (en) * 2012-12-28 2014-07-10 Miyoshi Oil & Fat Co Ltd Novel gemini compound and production method thereof, and cationic surfactant and dispersant that use the novel gemini compound
CN104801233A (en) * 2014-12-16 2015-07-29 江南大学 Viscoelastic solution containing trimeric anionic surfactant component and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102167673A (en) * 2011-03-14 2011-08-31 广东工业大学 Surfactant containing adamantane and preparation method thereof
CN102899901A (en) * 2012-10-23 2013-01-30 金发科技股份有限公司 High-temperature-resistant emulsion type carbon fiber sizing agent and preparation and applications of carbon fiber sizing agent
JP2014129302A (en) * 2012-12-28 2014-07-10 Miyoshi Oil & Fat Co Ltd Novel gemini compound and production method thereof, and cationic surfactant and dispersant that use the novel gemini compound
CN104801233A (en) * 2014-12-16 2015-07-29 江南大学 Viscoelastic solution containing trimeric anionic surfactant component and preparation method thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106588708A (en) * 2016-11-18 2017-04-26 塔里木大学 Method for synthesizing Gemini surfactant
CN108047098A (en) * 2016-11-18 2018-05-18 塔里木大学 The method for synthesizing Gemini surface active agent
CN108117498A (en) * 2016-11-18 2018-06-05 塔里木大学 A kind of synthetic method of Gemini surface active agent
CN108117498B (en) * 2016-11-18 2020-04-07 塔里木大学 Synthesis method of gemini surfactant
CN108047098B (en) * 2016-11-18 2020-04-07 塔里木大学 Method for synthesizing gemini surfactant
CN108837773A (en) * 2018-06-20 2018-11-20 江南大学 A kind of viscoelastic solution formed by abietyl dipeptides surfactant

Also Published As

Publication number Publication date
CN105879772B (en) 2017-10-10

Similar Documents

Publication Publication Date Title
CN101502772A (en) Colophony-based sulphonate type gemini surfactant and method for preparing the same
CN103555345A (en) Preparation and application of novel liquid crystal compound
CN103130675A (en) Industrial production method of high-purity N-lauroyl-L-alanine surfactant
CN105879772A (en) Trimeric anionic surfactant with long rigid linking group and viscoelastic solution formed by trimeric anionic surfactant
CN105435706A (en) Sulfonate-type anion dimeric surfactant and preparation method thereof
CN102516064A (en) Preparation method of nonionic-anionic compound type surfactant and application thereof
CN101480590B (en) Sulphonate Gemini surfactant and preparation method thereof
CN103611471B (en) One class contains carboxylate surface active agent of aromatic group and preparation method thereof
CN1850795A (en) Bialkylbiphenyl sodium disulfonate, and its preparing method
CN108863840A (en) The fluorinated derivatives and preparation method thereof of azo-based benzene
CN108837773A (en) A kind of viscoelastic solution formed by abietyl dipeptides surfactant
CN102618242A (en) Oil-displacing agent as Gemini surfactant
CN107088386B (en) A kind of Long carbon chain carboxylate surface active agent of high-dissolvability and its viscoelastic solution of formation
CN112175597A (en) Well-flushing foam water shutoff agent and preparation method thereof
CN103736422B (en) Fluorocarbon surfactant for organic oil phases
CN109054795B (en) Preparation method of hybrid fluorine-containing surfactant for ultra-low permeability reservoir flooding
CN103242855A (en) Liquid crystal compound containing cyclobutyl and difluorometheneoxy
CN104801233B (en) A kind of viscoelastic solution and preparation method who contains trimerization anion surface active agent composition
CN103374344B (en) After a kind of broken glue, there is surface-active fracturing fluid system
CN102728272A (en) Cashew-based quaternary ammonium salt cationic surfactant and its preparation method
CN108854838B (en) A kind of abietyl lactic acid surfactant and its application
CN101792407A (en) Method for preparing 1-aryl ethanesulfonic acid
CN103965063B (en) Sarpogrelate hydrochloride new preparation process
CN103193835A (en) Novel method for synthesizing and purifying sucrose octasulphonate sodium salt
JPH03505093A (en) Fluorinated 4″-cyano-substituted terphenyl

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right

Effective date of registration: 20201208

Address after: 257000 Shandong province Dongying city Dongying port economic development area seaport road to the north and west of Donggang Road

Patentee after: SHANDONG DAMING FINE CHEMICAL Co.,Ltd.

Address before: Room 2513, Huayuan Jinyue Center office building, 415 Taihua North Road, Weiyang District, Xi'an City, Shaanxi Province 710000

Patentee before: Jiuer (Xi'an) Intellectual Property Service Co.,Ltd.

Effective date of registration: 20201208

Address after: Room 2513, Huayuan Jinyue Center office building, 415 Taihua North Road, Weiyang District, Xi'an City, Shaanxi Province 710000

Patentee after: Jiuer (Xi'an) Intellectual Property Service Co.,Ltd.

Address before: No. 1800 road 214122 Jiangsu Lihu Binhu District City of Wuxi Province

Patentee before: Jiangnan University

TR01 Transfer of patent right