CN104478755A - Preparation method of polymerizable zwitterionic surfactant - Google Patents
Preparation method of polymerizable zwitterionic surfactant Download PDFInfo
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- CN104478755A CN104478755A CN201410768693.9A CN201410768693A CN104478755A CN 104478755 A CN104478755 A CN 104478755A CN 201410768693 A CN201410768693 A CN 201410768693A CN 104478755 A CN104478755 A CN 104478755A
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- acrylamide
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- polymerizable
- zwitterionics
- dimethylaminoethyl
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Abstract
The invention relates to a preparation method of a polymerizable zwitterionic surfactant. The preparation method of the polymerizable zwitterionic surfactant comprises the following steps: adding a certain amount of N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino propyl) acrylamide and C5-11 linear-chain bromo carboxylic acid into a reaction flask, by taking potassium iodide as a catalyst and taking absolute ethyl alcohol or acetone as a solvent, putting the reaction flask in a water bath kettle, magnetically stirring, and continuing to react under the protection of nitrogen; filtering products, carrying out rotary evaporation on filtrate to remove ethyl alcohol or acetone, then adding water to dissolve, and repeatedly extracting by using diethyl ether; freezing and pumping off water phase to obtain white powder which is the polymerizable zwitterionic surfactant. The preparation method of the polymerizable zwitterionic surfactant has the most important characteristics of no polymerization inhibitor and low reaction temperature; the catalyst is added, so that the reaction rate is increased; the water is frozen and removed, so that the separation is facilitated.
Description
Technical field
The present invention relates to a kind of preparation method of polymerizable zwitterionics; Belong to organic compound preparation technical field.
Background technology
Polymerizable zwitterionics is also referred to as zwitter-ion surface active monomer, its structure is generally made up of the unsaturated link(age) part with polymerization activity and the pendant side group moiety with electric neutrality bisexual ion purification feature, by the homopolymerization under certain condition of these monomers or with other neutral monomer copolymerization can obtain net charge be zero, the amphoteric ion polymer with anti-polyelectrolyte solution behavior.Amphoteric ion polymer it there is excellent chemical resistant properties, thermostability, hydratability and be not subject to the features such as solution ph impact.Be expected to obtain important application in oilfield exploitation, water treatment, weaving, medicine, turbulent flow drag reduction and colloid protection etc.This base polymer is as having good temperature resistance salt tolerant, anti-collapse and control geology yield during additive for drilling fluid.
Appearing in the newspapers in aggretion type zwitterionics kind, to lead maximum should be betaine type amphoteric monomer.Usually carboxylic acid betaine type and 2 kinds, sulphonic acid betaine type is had.Ladenheim H. has prepared polyvinyl sultaine amphoterics (Journal of Polymer Science 1957 the earliest, 26 (113): 251 – 254), Hart R. tertiary amine and l, 4-fourth sultone reacts, obtain polymer monomer (Hart R.and D.Timmerman.Journal of Polymer Science.1958,28 (118) 638 – 640).
People's 4-vinylpridines and 1 such as Gui Zhangliang, 3-propane sultone has synthesized drone salt in 4-vinyl-1-(3-sulfopropyl) pyridine, radical copolymerization is carried out with AM monomer, obtain sulphonic acid betaine amphoteric ion copolymer (the osmanthus Zhang Liang simultaneously containing negative ions group, safe good fortune, Zeng Junxi, etc. polymer journal, 2009, (4): 363-368.); The people such as Ding Wei are Material synthesis sulfobetaine type two sexual function (applied chemistry, 2011,28 (5) 555-558) with acrylamide propyl-dimethyl amine (DMAPAA) and 1,3-propyl group sultone.The people such as Deng Mingan have synthesized a kind of carboxylic acid beet alkali ampholytic ion monomer 2-(2-methylacryoyloxyethyl dimethylin) acetate (DMAC).It and acrylamide have synthesized the ampholyte copolymer containing carboxylic acid betaine group of series of novel, find that this multipolymer has obvious anti-polyelectrolyte solution behavior, and than the multipolymer only containing a kind of ion, there is good salt tolerant, heat resistance (Zhong Shan Imperial College journal (natural science edition), 2001,40 (1): 121-124).
Current ionic surface active agent, in preparation process, needs to add the plurality of reagents such as stopper, and speed of response is slow, and technique is loaded down with trivial details.
Summary of the invention
The object of this invention is to provide a kind of preparation method of polymerizable zwitterionics; Solve the problem of complicated process of preparation in prior art.
Technical scheme of the present invention comprises the steps:
N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide is added in reaction flask, the straight chain bromo carboxylic acid of 5-11 carbon, potassiumiodide makees catalyzer, dehydrated alcohol or acetone as solvent, be placed in the water-bath of certain temperature, magnetic agitation, under nitrogen protection sustained reaction certain hour; Filtered by product, filtrate, by rotary evaporation removing ethanol or acetone, then adds suitable quantity of water and dissolves, repeatedly extract with ether; Aqueous phase is freezing drains to obtain white powder, is product.
Described N-(2-dimethylaminoethyl) acrylamide or the mol ratio of N-(2-dimethylamino-propyl) acrylamide and bromo carboxylic acid are 1:1-1.5.
The straight chain bromo carboxylic acid of 5-11 described carbon is respectively that 5-bromine valeric acid, 6-bromocaproic acid, 7-bromine enanthic acid, 8-bromine are sad, 9-bromine n-nonanoic acid, 10-bromine capric acid and 11-bromine undeeanoic acid.
Described KI catalyst levels is the 1-2% of N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide quality.
Described ethanol or acetone solvent consumption and N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide ratio are that N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide amount of substance are 1.75 × 10
-2-2 × 10
-2mol, ethanol or acetone are 10-20ml.
Adding the amount of water and N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide ratio after described filtration evaporation is that N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide amount of substance are 1.75 × 10
-2-2 × 10
-2mol, water is 10-20ml.
Temperature of reaction in described water-bath is 30-45 DEG C.
Described sustained reaction 50-72h under nitrogen protection.
Described ether consumption be responseless reactant is all extracted till.
Maximum feature of the present invention to add stopper, and temperature of reaction is low, adds catalyzer to improve speed of response, freezingly dewaters, and is convenient to be separated.
Embodiment
The present invention is illustrated by the following examples.
Preparation method's reaction formula of a kind of polymerizable of the present invention zwitterionics is as follows:
Embodiment 1
2g N-(2-dimethylaminoethyl) acrylamide, 3.18g 5-bromo valeric acid are placed in there-necked flask, add 0.02g KI, 10ml acetone; pass into N2, under N2 protection, constant temperature 30 DEG C reaction 60h; filter, filtrate is revolved and is steamed removing acetone, is then dissolved in water; by extracted with diethyl ether; remove unreacted reactant, utilize freezing draining to dewater completely after separation, obtain white powder; be product, yield is 50.4%.
Embodiment 2
2g N-(2-dimethylaminoethyl) acrylamide, 4g 5-bromo valeric acid are placed in there-necked flask, add 0.03g KI, 15ml ethanol; pass into N2, under N2 protection, constant temperature 45 DEG C reaction 72h; filter, filtrate is revolved and is steamed removing ethanol, is then dissolved in water; by extracted with diethyl ether; remove unreacted reactant, utilize freezing draining to dewater completely after separation, obtain white powder; be product, yield is 72.3%.
Embodiment 3
2g N-(2-dimethylamino-propyl) acrylamide, 7g 5-bromo-undecanoic acid are placed in there-necked flask, add 0.03g KI, 15ml ethanol; pass into N2, under N2 protection, constant temperature 40 DEG C reaction 66h; filter, filtrate is revolved and is steamed removing ethanol, is then dissolved in water; by extracted with diethyl ether; remove unreacted reactant, utilize freezing draining to dewater completely after separation, obtain white powder; be product, yield is 65.8%.
Embodiment 4
2g N-(2-dimethylamino-propyl) acrylamide, 7.5g 5-bromo-undecanoic acid are placed in there-necked flask, add 0.04g KI, 15ml acetone; pass into N2, under N2 protection, constant temperature 45 DEG C reaction 72h; filter, filtrate is revolved and is steamed removing acetone, is then dissolved in water; by extracted with diethyl ether; remove unreacted reactant, utilize freezing draining to dewater completely after separation, obtain white powder; be product, yield is 71.3%.
Embodiment 5
N-(2-dimethylaminoethyl) acrylamide is added in reaction flask, 6-bromocaproic acid, N-(2-dimethylaminoethyl) acrylamide and 6-bromocaproic acid mol ratio are 1:1, potassiumiodide makees catalyzer, KI catalyst levels is 1% of N-(2-dimethylaminoethyl) acrylamide quality, solvent made by dehydrated alcohol, ethanol consumption and N-(2-dimethylaminoethyl) acrylamide ratio are that N-(2-dimethylaminoethyl) acrylamide amount of substance is 1.75 × 10
-2mol, ethanol is 10ml; Be placed in the water-bath of 45 DEG C, magnetic agitation, under nitrogen protection sustained reaction 50h; By product filter, filtrate removes ethanol by rotary evaporation, then adds 10ml water dissolution, repeatedly extracts with ether, ether consumption be responseless reactant is all extracted till; Aqueous phase is freezing drains to obtain white powder, is product.
Embodiment 6
In reaction flask, add N-(2-dimethylamino-propyl) acrylamide, 7-bromine enanthic acid, N-(2-dimethylamino-propyl) acrylamide and 7-bromine enanthic acid mol ratio are 1:1.5; Potassiumiodide makees catalyzer, and KI catalyst levels is 2% of N-(2-dimethylamino-propyl) acrylamide quality; Acetone as solvent, acetone solvent consumption and N-(2-dimethylamino-propyl) acrylamide ratio are that N-(2-dimethylamino-propyl) acrylamide amount of substance is 2 × 10
-2mol, acetone is 20ml, is placed in the water-bath of 30 DEG C, magnetic agitation, under nitrogen protection sustained reaction 72h; Filtered by product, filtrate removes acetone by rotary evaporation, then adds 20ml water dissolution, repeatedly extracts with ether; Aqueous phase is freezing drains to obtain white powder, is product.
5-bromine valeric acid described in embodiment of the present invention 1-6,6-bromocaproic acid, 7-bromine enanthic acid also can be replaced that 8-bromine is sad, 9-bromine n-nonanoic acid, 10-bromine capric acid or 11-bromine undeeanoic acid.Above about specific descriptions of the present invention, be only not limited to the technical scheme described by the embodiment of the present invention for illustration of the present invention.Those of ordinary skill in the art should be appreciated that and still can modify to the present invention or equivalent replacement, to reach identical technique effect.Needs are used, all in protection scope of the present invention as long as meet.
Claims (9)
1. the preparation method of a polymerizable zwitterionics, it is characterized in that comprising the steps: in reaction flask, add N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide, the straight chain bromo carboxylic acid of 5-11 carbon, potassiumiodide makees catalyzer, dehydrated alcohol or acetone as solvent, be placed in the water-bath of certain temperature, magnetic agitation, under nitrogen protection sustained reaction certain hour; Filtered by product, filtrate, by rotary evaporation removing ethanol or acetone, then adds suitable quantity of water and dissolves, repeatedly extract with ether; Aqueous phase is freezing drains to obtain white powder, is product.
2. the preparation method of a kind of polymerizable zwitterionics according to claim 1, is characterized in that the mol ratio of described N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide and bromo carboxylic acid is 1:1-1.5.
3. the preparation method of a kind of polymerizable zwitterionics according to claim 1, is characterized in that the straight chain bromo carboxylic acid of a described 5-11 carbon is respectively that 5-bromine valeric acid, 6-bromocaproic acid, 7-bromine enanthic acid, 8-bromine are sad, 9-bromine n-nonanoic acid, 10-bromine capric acid and 11-bromine undeeanoic acid.
4. the preparation method of a kind of polymerizable zwitterionics according to claim 1, is characterized in that described KI catalyst levels is the 1-2% of N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide quality.
5. the preparation method of a kind of polymerizable zwitterionics according to claim 1, it is characterized in that described ethanol or acetone solvent consumption and N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide ratio are that N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide amount of substance are 1.75 × 10
-2-2 × 10
-2mol, ethanol or acetone are 10-20ml.
6. the preparation method of a kind of polymerizable zwitterionics according to claim 1, adding the amount of water and N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide ratio after it is characterized in that described filtration evaporation is that N-(2-dimethylaminoethyl) acrylamide or N-(2-dimethylamino-propyl) acrylamide amount of substance are 1.75 × 10
-2-2 × 10
-2mol, water is 10-20ml.
7. the preparation method of a kind of polymerizable zwitterionics according to claim 1, is characterized in that the temperature of reaction in described water-bath is 30-45 DEG C.
8. the preparation method of a kind of polymerizable zwitterionics according to claim 1, is characterized in that described sustained reaction 50-72h under nitrogen protection.
9. the preparation method of a kind of polymerizable zwitterionics according to claim 1, it is characterized in that described ether consumption be responseless reactant is all extracted till.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57197250A (en) * | 1981-05-29 | 1982-12-03 | Taisei Kako Kk | Preparation of monomeric mixture containing n-isopropoxymethylacrylamide essentially |
| CN1935346A (en) * | 2006-09-22 | 2007-03-28 | 西南石油大学 | Bisamide bissulfosalt double surface active agent, and its synthesizing method |
| CN101143832A (en) * | 2007-09-30 | 2008-03-19 | 浙江工业大学 | Method for preparing N,N-dialkylacrylamide |
| CN101628214A (en) * | 2009-07-25 | 2010-01-20 | 大连理工大学 | Acrylamide polymerizable emulsifier with cations and non-ions and preparation method thereof |
-
2014
- 2014-12-12 CN CN201410768693.9A patent/CN104478755A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57197250A (en) * | 1981-05-29 | 1982-12-03 | Taisei Kako Kk | Preparation of monomeric mixture containing n-isopropoxymethylacrylamide essentially |
| CN1935346A (en) * | 2006-09-22 | 2007-03-28 | 西南石油大学 | Bisamide bissulfosalt double surface active agent, and its synthesizing method |
| CN101143832A (en) * | 2007-09-30 | 2008-03-19 | 浙江工业大学 | Method for preparing N,N-dialkylacrylamide |
| CN101628214A (en) * | 2009-07-25 | 2010-01-20 | 大连理工大学 | Acrylamide polymerizable emulsifier with cations and non-ions and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 丁伟 等: "新型功能单体溴化甲基丙烯酰氧乙基二甲基羧壬基铵的合成与表征", 《应用化学》, vol. 23, no. 8, 31 August 2006 (2006-08-31) * |
| 丁伟 等: "甜菜碱型两性离子聚合物P(AM-DMAPAAS)的盐溶液性质", 《应用化学》, vol. 28, no. 5, 31 May 2011 (2011-05-31) * |
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Application publication date: 20150401 |