CN108821627A - Anti- mud agent of a kind of gemini quaternary ammonium salt containing xenyl and preparation method and application - Google Patents
Anti- mud agent of a kind of gemini quaternary ammonium salt containing xenyl and preparation method and application Download PDFInfo
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- CN108821627A CN108821627A CN201810678953.1A CN201810678953A CN108821627A CN 108821627 A CN108821627 A CN 108821627A CN 201810678953 A CN201810678953 A CN 201810678953A CN 108821627 A CN108821627 A CN 108821627A
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- mud
- agent
- preparation
- ammonium salt
- quaternary ammonium
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/005—Halogen-containing compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The preparation method of a kind of anti-mud agent of gemini quaternary ammonium salt containing xenyl and such compound, such being structurally characterized in that for anti-mud agent are connected to two symmetrical alkyl tertiary amines by quaternization reaction at the both ends of biphenyl-benzyl dichloride, and the preparation method of the anti-mud agent is：Using biphenyl-benzyl dichloride and alkyl tertiary amine as raw material, after being dissolved in organic solvent, under conditions of 60-75 DEG C, it is prepared through quaternization reaction, the raw material that the preparation method of this kind of anti-mud agent is related to is cheap and easy to get, reaction condition is mild, synthesis step is simple, easy post-processing, it is compounded with polycarboxylic acids dehydragent and the anti-mud performance of cement can be improved, and there is good compatibility with polycarboxylate water-reducer, when montmorillonite content is 1%, anti- mud agent volume is 0.1 ‰, by itself and polycarboxylic acids water reducing agent compositional, the initial paste flowing degree of cement reaches 280mm, than improving 30mm before not compounding, flowing degree of net paste of cement is 270mm when 2h, loss late is 3.5%.The anti-mud time is long and stability is good, safety and environmental protection, is suitable for large-scale application.
Description
Technical field
The present invention relates to concrete admixture and technical field of surfactant, in particular to a kind of season of Shuangzi containing xenyl
Anti- mud agent of ammonium salt and preparation method and application.
Background technique
Polycarboxylate dehydragent have high water reducing rate, high-thin arch dam, it is environmentally protective the advantages that, therefore in engineering concrete at
For essential external application additive.But it is sensitive to aggregate clay content, especially the soil in sandstone, and wherein sandstone includes natural
Sand and Machine-made Sand.In recent years, the exploitation due to people to natural sand stone causes good sandstone raw material exhausted, so turning machine
Sand processed.And Machine-made Sand corner angle are big, rough surface, clay content and mountain flour amount are high, are easier to the Free water and water-reducing agent of absorption system, lead
The just opposite reduction of the adsorbable effective water-reducing agent of cement institute and Free water is caused, very big influence is caused to its fluidity.Research hair
Montmorillonite in existing clay is maximum to the negative effect of water-reducing agent.The major measure taken at present has washing aggregate, but destroys bone
Expect structure, and is not easy to realize in construction；Secondly the water-reducing agent of excess is mixed, but will cause concrete water bleeding, isolates, collapses to it
Degree and intensity adversely affect；It is compounded also by anti-mud external application additive with water-reducing agent, reaches anti-mud effect.
Summary of the invention
In order to overcome the above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of gemini quaternary ammonium salts containing xenyl
Anti- mud agent and preparation method and application has synthesis technology simple, and raw material is cheap and easy to get, the spy suitable for large-scale production
Point.
To achieve the goals above, the technical solution adopted by the present invention is that：
Two alkyl tertiary amine monomers are introduced connection by quaternization reaction by a kind of anti-mud agent of gemini quaternary ammonium salt containing xenyl
The both ends of benzene benzyl dichloride, with structure below：
Wherein：R is-CH3Or-CH2-CH3。
A kind of preparation method of the anti-mud agent of gemini quaternary ammonium salt containing xenyl, this method specifically include following steps：
Step 1：Biphenyl-benzyl dichloride, alkyl tertiary amine and organic are added in the three-necked flask equipped with stirring rod and condenser pipe
Solvent, heating carry out quaternization reaction.After reaction, mixed liquor I is obtained；
Step 2：The mixed liquor I is filtered to remove extra organic solvent, obtains crude product II；
Step 3：The crude product II is mixed using ethyl acetate and is precipitated, filtered, dried and can be obtained containing biphenyl
The anti-mud agent of base gemini quaternary ammonium salt.
Alkyl tertiary amine in the step 1 is trimethylamine or triethylamine.
The molar ratio of biphenyl-benzyl dichloride and alkyl tertiary amine in the step 1 is 1:2~2.2, reaction raw materials with have
The mass ratio of solvent is 1:1~1.5.
Reaction temperature in the step 1 is 60~80 DEG C, and the reaction time is 6~8 hours.
Organic solvent in the step 1 include acetone, N,N-dimethylformamide, ethyl alcohol, tetrahydrofuran, in chloroform
Any one or two or more combinations；Preferably, the organic solvent is selected from ethyl alcohol or acetone.
Beneficial effects of the present invention：
1, the anti-mud agent of gemini quaternary ammonium salt containing xenyl proposed is invented, synthesis technology is simple, and raw material is cheap and easy to get, instead
Mild condition is answered, well, environmentally protective and no pollution to the environment, yield is high, is suitable for large-scale production.
2, the anti-mud agent of gemini quaternary ammonium salt containing xenyl proposed is invented, compared with prior art, application method is simple,
Be diluted with water, earth surfaces strong adsorption and stability it is good, and dosage is few, and using effect is good.Contain in montmorillonite
When amount is 1%, anti-mud agent volume is 0.1 ‰, it is multiple with polycarboxylate water-reducer (rolling over solid volume is the 0.2% of cement quality)
Match, the initial paste flowing degree of cement reaches 280mm, and than improving 30mm before not compounding, flowing degree of net paste of cement is when 2h
270mm, loss late 3.5%.The anti-mud time is long and stability is good, safety and environmental protection, is suitable for large-scale application.
Specific embodiment
Below with reference to embodiment, invention is further described in detail.
One, embodiment is prepared
Embodiment 1
(1) be added in the three-necked flask equipped with stirring rod and condenser pipe 17.5g biphenyl-benzyl dichloride (100mmol),
20.24g triethylamine (200mmol) and 39.72ml organic solvent n,N-Dimethylformamide are warming up to 60 DEG C, carry out quaternary ammonium
Change 6 hours of reaction obtain mixed liquor I after reaction；
(2) mixed liquor I is obtained into crude product II using extra n,N-Dimethylformamide is filtered to remove；
(3) crude product II is precipitated using ethyl acetate, is filtered, dries the season of Shuangzi containing xenyl can be obtained
The anti-mud agent of ammonium salt, yield 86%.
Embodiment 2
(1) be added in the three-necked flask equipped with stirring rod and condenser pipe 17.5g biphenyl-benzyl dichloride (100mmol),
22.25g triethylamine (220mmol) and 49ml organic solvent-acetone are warming up to 70 DEG C, carry out 7 hours of quaternization reaction.Instead
After answering, mixed liquor I is obtained；
(2) mixed liquor I is obtained into crude product II using extra acetone is filtered to remove；
(3) crude product II is precipitated using ethyl acetate, is filtered, dries the season of Shuangzi containing xenyl can be obtained
The anti-mud agent of ammonium salt, yield 89%.
Embodiment 3
(1) be added in the three-necked flask equipped with stirring rod and condenser pipe 17.5g biphenyl-benzyl dichloride (100mmol),
29.25g triethylamine (220mmol) and 74ml organic solvent ethyl alcohol are warming up to 75 DEG C, carry out 8 hours of quaternization reaction, instead
After answering, mixed liquor I is obtained；
(2) mixed liquor I is obtained into crude product II using extra ethyl alcohol is filtered to remove；
(3) crude product II is precipitated using ethyl acetate, is filtered, dries the season of Shuangzi containing xenyl can be obtained
The anti-mud agent of ammonium salt, yield 91%.
Embodiment 4
(1) be added in the three-necked flask equipped with stirring rod and condenser pipe 17.5g biphenyl-benzyl dichloride (100mmol),
29.25g triethylamine (220mmol) and 49ml organic solvent-acetone are warming up to 75 DEG C, carry out 8 hours of quaternization reaction.Instead
After answering, mixed liquor I is obtained；
(2) mixed liquor I is obtained into crude product II using extra acetone is filtered to remove；
(3) crude product II is precipitated using ethyl acetate, is filtered, dries the season of Shuangzi containing xenyl can be obtained
The anti-mud agent of ammonium salt, yield 87%.
Current main additive is the anti-mud agent of small organic molecule, can be preferentially adsorbed in montmorillonite, its activity is occupied
Site is adsorbed on the water-reducing agent being added more on cement and reaches dispersion purpose.The anti-mud agent of small organic molecule mainly include yin from
Subtype and cationic.Due to being elecrtonegativity after montmorillonite water suction, cation is added can be by electrostatic attraction strong adsorption in table
Face and interlayer prevent its water swelling, and biphenyl structural area coverage is big, shield its Absorptive complex wave to water-reducing agent, and can enter
Interlayer reduces it and adsorbs to water-reducing agent intercalation, weakens montmorillonite to the negative effect of slurry.
Based on the clay composition in montmorillonite simulation concrete, the present invention provides a series of short chain quaternary ammoniums of Shuangzi cations
Salt is as anti-mud agent, to the inhibitory effect of montmorillonite after compounding with water-reducing agent.Pass through the test of the paste flowing degree of cement, hair
The now anti-mud agent of the series has obviously effect.
Two, anti-mud effect
Gemini quaternary ammonium salt containing xenyl is compounded with the water-reducing agent that market is sold, gemini quaternary ammonium salt respectively first to mix,
With mixing, after the mode mixed compounded with polycarboxylate water-reducer, tested by flowing degree of net paste of cement, as a result, it has been found that Shuangzi quaternary ammonium
The anti-mud effect that salt can be performed better than in a manner of first mixing with polycarboxylic acids water reducing agent compositional.At room temperature, net by test cement
Slurry fluidity carrys out paste flowing degree of the anti-mud agent prepared in embodiment 1,2,3,4 under 1% montmorillonite.It sends out afterwards after tested
It is existing：When montmorillonite content is 1%, anti-mud agent volume is 0.1 ‰, and by it, (rolling over solid volume is cementaceous with polycarboxylate water-reducer
The 0.2% of amount) compounding, the initial paste flowing degree of cement is respectively 265mm, 270mm, 280mm, 275mm.The paste flowing degree of 2h
For 240mm, 250mm, 275mm, 255mm, the anti-mud time is long and stability is good, and the anti-mud performance of embodiment 3 is best.In addition, through
When montmorillonite content increases, the anti-mud effect of such anti-mud agent is still good for test.Since reaction raw materials are cheap and easy to get, reaction
Mild condition, synthesis step is simple, easy post-processing, safety and environmental protection, is suitable for large-scale application.
Claims (7)
1. a kind of anti-mud agent of gemini quaternary ammonium salt containing xenyl, which is characterized in that by quaternization reaction, by two alkyl tertiary amine lists
Body introduces the both ends of biphenyl-benzyl dichloride, with structure below：
Wherein：R is-CH3Or-CH2-CH3。
2. the preparation method based on anti-mud agent described in claim 1, which is characterized in that include the following steps：
Step 1：Biphenyl-benzyl dichloride, alkyl tertiary amine and organic molten are added in the three-necked flask equipped with stirring rod and condenser pipe
Agent, heating carry out quaternization reaction and obtain mixed liquor I after reaction；
Step 2：By the mixed liquor I using extra organic solvent is filtered to remove, crude product II is obtained；
Step 3：The crude product II is mixed using ethyl acetate and is precipitated, filtered, dry can be obtained it is double containing xenyl
The sub- anti-mud agent of quaternary ammonium salt.
3. a kind of preparation method of the anti-mud agent of gemini quaternary ammonium salt containing xenyl according to claim 2, which is characterized in that institute
The molar ratio for stating the biphenyl-benzyl dichloride and alkyl tertiary amine in step 1 is 1:2~2.2, the matter of reaction raw materials and organic solvent
Amount is than being 1:1~1.5.
4. a kind of preparation method of the anti-mud agent of gemini quaternary ammonium salt containing xenyl according to claim 2, which is characterized in that institute
Stating the reaction temperature in step 1 is 60~80 DEG C, and the reaction time is 6~8 hours.
5. a kind of preparation method of the anti-mud agent of gemini quaternary ammonium salt containing xenyl according to claim 2, which is characterized in that institute
State the organic solvent in step 1 include acetone, N,N-dimethylformamide, ethyl alcohol, tetrahydrofuran, in chloroform any one or
Two or more combinations；Preferably, the organic solvent is selected from ethyl alcohol or acetone.
6. a kind of preparation method of the anti-mud agent of gemini quaternary ammonium salt containing xenyl according to claim 2, which is characterized in that institute
Stating the alkyl tertiary amine in step 1 is trimethylamine or triethylamine.
7. a kind of anti-mud agent containing xenyl according to claim 1 or 2 and it is applied to concrete external application additive agent field,
Anti- mud effect is improved with polycarboxylic acids water reducing agent compositional.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810678953.1A CN108821627A (en) | 2018-06-27 | 2018-06-27 | Anti- mud agent of a kind of gemini quaternary ammonium salt containing xenyl and preparation method and application |
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| CN201810678953.1A CN108821627A (en) | 2018-06-27 | 2018-06-27 | Anti- mud agent of a kind of gemini quaternary ammonium salt containing xenyl and preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734612A (en) * | 2018-12-14 | 2019-05-10 | 陕西科技大学 | A kind of end tetrahydroxy gemini quaternary ammonium salt, preparation method and application |
| CN110981278A (en) * | 2019-12-30 | 2020-04-10 | 三一筑工科技有限公司 | Concrete admixture and use method thereof |
-
2018
- 2018-06-27 CN CN201810678953.1A patent/CN108821627A/en active Pending
Non-Patent Citations (5)
| Title |
|---|
| R. A. ZHELDAKOVA: "《Synthesis, Antimicrobial and Antifungal Activity of Double Quaternary Ammonium Salts of Biphenyls》", 《JOURNAL OF GENERAL CHEMISTRY》 * |
| 张轩等: "新型双子季铵盐的合成及粘土防膨性能评价", 《石油与天然气化工》 * |
| 李刚森等: "季铵盐双子表面活性剂N,N’-双(十二/十四烷基二甲基)-1,4-对苯二甲基氯化铵盐的合成及性能", 《精细化工》 * |
| 王方刚等: "改善聚羧酸超塑化剂与蒙脱土适应性的抗泥剂及其机理研究", 《建筑材料学报》 * |
| 黎锦霞等: "《季铵盐型抗泥剂的合成及其性能研究》", 《广东建材》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109734612A (en) * | 2018-12-14 | 2019-05-10 | 陕西科技大学 | A kind of end tetrahydroxy gemini quaternary ammonium salt, preparation method and application |
| CN110981278A (en) * | 2019-12-30 | 2020-04-10 | 三一筑工科技有限公司 | Concrete admixture and use method thereof |
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Application publication date: 20181116 |
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