CN101864049A - Preparation method of high-molecular surface active agent - Google Patents
Preparation method of high-molecular surface active agent Download PDFInfo
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Abstract
The invention relates to a preparation method of high-molecular surface active agent, which is characterized in that: 2 - {[(dodecyl thio) formyl thio] thio} succinic acid alkyl, acrylic acid, absolute ethyl alcohol are reacted with 4, 4'-azo-bis (4 - cyano acid) under the protection of argon gas at the temperature of 55 to 95 DEG C to obtain polyacrylic acid; absolute ethyl alcohol, 4, 4'-azo-bis (4 - cyano acid) and butyl acrylate are added in the polyacrylic acid, the temperature is increased to 55 to 95 DEG C to be reacted for 2 to 8 hours and to be decompressed and distilled after introducing argon gas, and wheat product, i.e. high-molecular surface active agent is obtained after being dried. The prepared molecular surface active agent not only can be used for emulsifying acrylate monomer, but also can be used as emulsifier for polymerizing emulsion. Amphipathy embedded copolymer is riveted on emulsion particles in the emulsion polymerization, and hydrophilic chain section extends into water phase, so the emulsion particles are stable through the space steric effect and the static effect so as to improve the electrolytic-resistant capacity and the frozen stability of the emulsion.
Description
Technical field
The present invention relates to a kind of preparation method of tensio-active agent, be specifically related to a kind of preparation method of polymeric surface active agent.
Background technology
Polymeric surface active agent is molecular weight more than thousands of and has surface-active material.Compare with low-molecular-weight surfactant, polymeric surface active agent has performances such as good dispersion, emulsification, thickening, stable and flocculation, is widely used at aspects such as viscosity increaser, flocculation agent, dispersion agent, emulsifying agent, emulsion splitter, solubilizing agent, wetting Agent for Printing Inks, static inhibitor, paper strengthening agents.
According to molecular structure and preparation method's classification, polymeric surface active agent mainly can be divided into graft type copolymer, block type multipolymer and random multipolymer.Wherein controlled to molecular weight, molecular weight distribution is narrower, the research of molecular structure and the programmable block type multipolymer of composition is one of pregnancy and challenging work in the polymer research field.The segmented copolymer that structure is clear and definite can show the character of a series of excellences, and such as in selective solvent, block polymer association can take place forms micella.So it is not only at the macromolecular solution theoretical side, and also has wide practical use in fields such as letex polymerization, life science, pharmacy and Materials science.
Rizzdao in 1998 etc. have reported a kind of novel active free radical polymerization.They adopt monomer polymerizations such as multiple pair of monothioester regulation and control vinylbenzene, vinylformic acid, methyl methacrylate under traditional radical initiator causes, the polymericular weight of gained raises and linear increasing with transformation efficiency; Molecular weight distributing index is then on a declining curve, and less than 1.3, has the feature of living polymerization.RAFT polymeric mechanism is to be that chain-transfer agent makes reversible chain transfer process rate surpass rate of chain growth greatly by thiocarbonic ester.This polymerization process comprises the reversible addition-fracture chain transfer reaction of a living chain, so be called the RAFT polymerization.
By RAFT polymerization synthetic polymkeric substance, the thiocarbonic acid SOH ester group on its chain-transfer agent is still stayed on the polymkeric substance, and it can be used as second kind of monomeric polymerization of macromolecular chain transfer agent regulation and control, forms the block polymer of compound with regular structure.(N Gaillard such as Gaillard, J Claverie, A Guyot.Progressin Organic Coatings, 2006,57:98-109.) (N Gaillard, A Guyot, J Claverie.Journal of Polymer Science:Part A:Polymer Chemistry, 2003,41:684-698.) use RAFT reagent C TA1 and CTA2 to synthesize butyl polyacrylate-b-polyacrylic acid segmented copolymer (PBA-b-PAA).Result of study shows molecular weight linear increase along with the increase of transformation efficiency of segmented copolymer, and near theoretical molecular, but molecular weight distribution broad (PDI is 1.8-1.9).
(M Save such as Save, M Manguian, C Chassenieux, et al.Macromolecules, 2005,38:280-289.) to use CTA3 to synthesize polystyrene-b-as chain-transfer agent by the mode of mass polymerization poly-to vinyl chloride segmented copolymer (PS-b-PVBC), obtains polystyrene-b-polyvinyl benzyltriethylammoinium chloride segmented copolymer (PS-b-P (VBTEAC)) after quaternized.Result of study shows that the experiment number-average molecular weight and the theoretical value of polymkeric substance are approaching, and number-average molecular weight linear increase with the increase of transformation efficiency, and molecular weight distributing index is lower than 1.3.
Garnier etc. (S Garnier, A Laschewsky.Macromolecules, 2005,38:7580-7592.) use the RAFT technology to synthesize with the amphipathic nature block polymer of butyl polyacrylate as the hydrophobicity block wetting ability block different with six kinds.At first, be that chain-transfer agent has synthesized butyl polyacrylate (CTA4) with thio phenyl acetate benzyl ester (BDTPhA).Afterwards, with six kinds of different hydrophilic monomer polymerizations of this butyl polyacrylate macromole RAFT reagent regulation and control, obtain six kinds of different segmented copolymers, as butyl polyacrylate-b-polyacrylamide pyrroles [poly (M1-b-M2)], polyacrylic acid-b-gathers N, N-DMAA [poly (M1-b-M2)], butyl polyacrylate-b-polyacrylic acid ethyl-methyl sulfoxide esters [poly (M1-b-M4)], butyl polyacrylate-b-polyacrylic acid ethylene glycol monomethyl ether ester [poly (M1-b-M5)], butyl polyacrylate-b-gathers N-1-sulfonic group-2-isopropyl methyl acrylamide [poly (M1-b-M6)], butyl polyacrylate-b-gathers N, N, the N-trimethylammonium third ammonium acrylamide [poly (M1-b-M7)].
(D E Ganeva such as Ganeva; E Sprong; H D Bruyn; et al.Macromolecules; 2007; 40:6181-6189.) with 2-{[(butyl sulfane base) the 2-thioformyl] the sulfane base propionic acid (CTA5) is that RAFT reagent sequential polymerization vinylformic acid and vinylbenzene obtain low-molecular-weight polyacrylic acid-b-polystyrene block copolymer, it can be used as the emulsifying agent of letex polymerization.(J F Zhou such as Zhou, L Wang, Q Yang, et al.J.Phys.Chem.B, 2007,111:5573-5580.) with S, S '-two diisopropyl acidic group trithiocarbonate (CTA6) has synthesized brush type amphipathic three block copolymer (molecular weight distributing index is 1.47-1.55) for RAFT reagent, this polymkeric substance has temperature and pH responsiveness.
Recently, caused the very big interest of academia in the application aspect the letex polymerization by RAFT polymerization synthetic amphipathic nature block polymer.(C J Ferguson such as Ferguson, R J Hughes, D Nguyen, etal.Macromolecules, 2005,38:2191-2204.) (C J Ferguson, R J Hughes, BT T Pham, et al.Macromolecules, 2002,35:9243-9245.) at first use a trithiocarbonate RAFT reagent to synthesize the water-soluble polypropylene acid block of short chain, regulate and control the polymerization of butyl acrylate then as macromole RAFT reagent.This multipolymer can self-assembly form micella in water, as the polymerization place of hydrophobic vinyl monomers.Manguian etc. (M Manguian, M Save, BCharleux.Macromol.Rapid Commun, 2006,27:399-404.) synthesized P (DEAEMA/H by a water-soluble RAFT reagent
+Cl
-)-b-PS polymeric surface active agent.Adopt similar method, and Santos etc. (A M dos Santos, J Pohn, M Lansalot, F D ' Agosto.Macromol.Rapid Commun, 2007,28:1325-1332.) with PEO-b-P (DMAEMA/H
+Cl
-)-RAFT is that emulsifying agent has synthesized polystyrene emulsion, and this emulsion has alkaline-resisting preferably stability and freeze-thawing resistant stability.
The active free radical polymerization especially utilization of RAFT polymerization technique provides an approach preferably for the block type polymer tensio-active agent that preparation has controlled architecture and estimated performance.People deepen continuously to the research of block type polymer tensio-active agent, develop the focus that new kind and new synthetic method are still current research.Because the block type polymer tensio-active agent is having broad prospects aspect emulsifier for emulsion polymerization, therefore synthetic the and application for it will more and more be subjected to domestic and international investigator's attention.
Up to now, various RAFT reagent comprise that dithiocarbonates or trithiocarbonate are synthesized and are applied in the middle of the controllable free-radical polymerisation.Because the controlled and living features of RAFT polymeric under suitable R AFT reagent and reaction conditions, can successfully prepare homopolymer and multipolymer.The amphipathic nature block polymer that adopts the RFAT method to obtain can be self-assembled into micella in selective solvent.Though two blocks and triblock copolymer have well been prepared by the RAFT method, current synthetic amphipathic di-block copolymer with narrow molecular weight distributions remains a kind of challenge.And the macromole RAFT reagent with narrow molecular weight distributions of synthesizing efficient is most important in the segmented copolymer of synthesizing amphipathic.
Summary of the invention
The object of the present invention is to provide a kind of preparation method that can prepare polymeric surface active agent with narrow molecular weight distributions.
For achieving the above object, the technical solution used in the present invention is: 1) at first by 1: (5-180): (50-7200): mol ratio (0.05-1) is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 55-95 ℃, under argon shield, react 2-8h, obtain polyacrylic acid;
2) and then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: the dehydrated alcohol of 50-7200 mole: 4 of 0.05-1 mole; 4 '-azo two (4-cyanopentanoic acid): the butyl acrylate of 5-180 mole adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 55-95 ℃; reaction 2-8h underpressure distillation promptly obtains light yellow product and is polymeric surface active agent after the drying under argon shield.
Prepared molecular surface active agent of the present invention (polyacrylic acid-b-butyl polyacrylate segmented copolymer) not only can also be used as the emulsifying agent of letex polymerization in order to the emulsion acrylic esters monomer.The amphipathic nature block polymer that the present invention obtains is to be anchored on emulsion particle in letex polymerization, and hydrophilic segment stretches to aqueous phase, make emulsion particle stable by space steric effect and electrostatic effect, thereby improved the ability and the freeze-thaw stability of emulsion electrolyte-resistant.Its rate of migration in polymeric film is starkly lower than low molecule emulsifying agent, has improved the performance of polymeric film.In addition, amphipathic nature block polymer also can change the surface topography of emulsion particle particle, finally influences the performance of emulsion.
Embodiment
Embodiment 1, at first by 1: 20: 120: 0.1 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 80 ℃, under argon shield, react 7h, obtain molecular weight distribution and be 1.03 polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 120 moles dehydrated alcohol: 0.1 mole 4; 4 '-azo two (4-cyanopentanoic acid): 20 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 80 ℃; reaction 7h underpressure distillation under argon shield promptly obtains molecular weight distribution and is 1.37 light yellow product and is polymeric surface active agent after the drying.Its CMC (micelle-forming concentration) is 7.75 * 10
-5G/mL.
Embodiment 2, at first by 1: 10: 200: 0.15 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 70 ℃, under argon shield, react 8h, obtain molecular weight distribution and be 1.03 polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 400 moles dehydrated alcohol: 0.15 mole 4; 4 '-azo two (4-cyanopentanoic acid): 30 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 70 ℃; reaction 8h underpressure distillation under argon shield promptly obtains molecular weight distribution and is 1.23 light yellow product and is polymeric surface active agent after the drying.Its CMC (micelle-forming concentration) is 6.32 * 10
-5G/mL.
Embodiment 3, at first by 1: 50: 500: 0.1 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 75 ℃, under argon shield, react 6h, obtain molecular weight distribution and be 1.06 polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 300 moles dehydrated alcohol: 0.2 mole 4; 4 '-azo two (4-cyanopentanoic acid): 30 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 75 ℃; reaction 6h underpressure distillation under argon shield promptly obtains molecular weight distribution and is 1.39 light yellow product and is polymeric surface active agent after the drying.Its CMC (micelle-forming concentration) is 5.20 * 10
-5G/mL.
Embodiment 4, at first by 1: 70: 700: 0.1 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 80 ℃, under argon shield, react 7h, obtain molecular weight distribution and be 1.07 polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 200 moles dehydrated alcohol: 0.15 mole 4; 4 '-azo two (4-cyanopentanoic acid): 20 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 80 ℃; reaction 7h underpressure distillation under argon shield promptly obtains molecular weight distribution and is 1.37 light yellow product and is polymeric surface active agent after the drying.Its CMC (micelle-forming concentration) is 7.47 * 10
-5G/mL.
Embodiment 5, at first by 1: 5: 50: 0.05 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 60 ℃, under argon shield, react 5h, obtain polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 50 moles dehydrated alcohol: 0.05 mole 4; 4 '-azo two (4-cyanopentanoic acid): 5 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 60 ℃; reaction 5h underpressure distillation promptly obtains light yellow product and is polymeric surface active agent after the drying under argon shield.
Embodiment 6, at first by 1: 120: 3000: 0.5 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 85 ℃, under argon shield, react 4h, obtain polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 4200 moles dehydrated alcohol: 0.6 mole 4; 4 '-azo two (4-cyanopentanoic acid): 130 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 85 ℃; reaction 4h underpressure distillation promptly obtains light yellow product and is polymeric surface active agent after the drying under argon shield.
Embodiment 7, at first by 1: 180: 7200: 1 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 95 ℃, under argon shield, react 2h, obtain polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 7200 moles dehydrated alcohol: 1 mole 4; 4 '-azo two (4-cyanopentanoic acid): 180 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 95 ℃; reaction 2h underpressure distillation promptly obtains light yellow product and is polymeric surface active agent after the drying under argon shield.
Embodiment 8, at first by 1: 150: 5000: 0.8 mol ratio is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 55 ℃, under argon shield, react 8h, obtain polyacrylic acid; And then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: 5500 moles dehydrated alcohol: 0.7 mole 4; 4 '-azo two (4-cyanopentanoic acid): 160 moles butyl acrylate adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 55 ℃; reaction 8h underpressure distillation promptly obtains light yellow product and is polymeric surface active agent after the drying under argon shield.
Claims (1)
1. the preparation method of a polymeric surface active agent is characterized in that:
1) at first by 1: (5-180): (50-7200): mol ratio (0.05-1) is with 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base } succsinic acid, vinylformic acid, dehydrated alcohol and 4,4 '-azo two (4-cyanopentanoic acid) adding is inserted with in the four-hole bottle of prolong, airway, thermometer, behind the logical argon gas temperature is risen to 55-95 ℃, under argon shield, react 2-8h, obtain polyacrylic acid;
2) and then in polyacrylic four-hole bottle is housed by 1 mole of 2-{[(dodecyl sulfenyl) thioformyl] the sulfane base succsinic acid: the dehydrated alcohol of 50-7200 mole: 4 of 0.05-1 mole; 4 '-azo two (4-cyanopentanoic acid): the butyl acrylate of 5-180 mole adds dehydrated alcohol, 4; 4 '-azo two (4-cyanopentanoic acid) and butyl acrylate; behind the logical argon gas temperature is risen to 55-95 ℃; reaction 2-8h underpressure distillation promptly obtains light yellow product and is polymeric surface active agent after the drying under argon shield.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102002136A (en) * | 2010-11-11 | 2011-04-06 | 陕西科技大学 | Method for preparing amphiphilic block copolymer with narrow molecular weight distribution |
| CN102274702A (en) * | 2011-05-10 | 2011-12-14 | 山东沃尔德科技发展有限公司 | Block macromolecular pigment dispersant, preparation method thereof, and pigment dispersion liquid containing dispersant |
| CN103483513A (en) * | 2013-09-09 | 2014-01-01 | 陕西科技大学 | Preparation method of fluorine-containing high-molecular surfactant |
| CN109988277A (en) * | 2019-04-22 | 2019-07-09 | 中南林业科技大学 | A method of AB block aqueous dispersion is prepared based on RAFT method |
| CN114621373A (en) * | 2021-06-10 | 2022-06-14 | 中国石油天然气集团有限公司 | Flocculant for oil-based drilling fluid and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102002136A (en) * | 2010-11-11 | 2011-04-06 | 陕西科技大学 | Method for preparing amphiphilic block copolymer with narrow molecular weight distribution |
| CN102274702A (en) * | 2011-05-10 | 2011-12-14 | 山东沃尔德科技发展有限公司 | Block macromolecular pigment dispersant, preparation method thereof, and pigment dispersion liquid containing dispersant |
| CN103483513A (en) * | 2013-09-09 | 2014-01-01 | 陕西科技大学 | Preparation method of fluorine-containing high-molecular surfactant |
| CN109988277A (en) * | 2019-04-22 | 2019-07-09 | 中南林业科技大学 | A method of AB block aqueous dispersion is prepared based on RAFT method |
| CN109988277B (en) * | 2019-04-22 | 2022-03-25 | 中南林业科技大学 | Method for preparing AB block water-based dispersant based on RAFT method |
| CN114621373A (en) * | 2021-06-10 | 2022-06-14 | 中国石油天然气集团有限公司 | Flocculant for oil-based drilling fluid and preparation method and application thereof |
| CN114621373B (en) * | 2021-06-10 | 2024-05-14 | 中国石油天然气集团有限公司 | Flocculant for oil-based drilling fluid and preparation method and application thereof |
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