CN102311368A - Twin-type wetting agent as well as preparation method and application thereof - Google Patents
Twin-type wetting agent as well as preparation method and application thereof Download PDFInfo
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- CN102311368A CN102311368A CN201110102268A CN201110102268A CN102311368A CN 102311368 A CN102311368 A CN 102311368A CN 201110102268 A CN201110102268 A CN 201110102268A CN 201110102268 A CN201110102268 A CN 201110102268A CN 102311368 A CN102311368 A CN 102311368A
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Abstract
The invention discloses a twin-type wetting agent as well as a preparation method and an application thereof. The twin-type wetting agent is of a structure of taking a plurality of methylene radicals as connecting radicals and containing bisamide and disulfonate. The preparation method of the twin-type wetting agent comprises the following steps of: acidylating fatty acid into fatty acyl chloride, then connecting two hydrophilic groups and two lipophilic groups via connecting groups, and then sulfonating the group to prepare the twin-type wetting agent. Good wetting effect is obtained by preparing the twin-type wetting agent into a water-based pesticide preparation, which can increase the spreadability of the pesticide preparation on the fertilizing surface and improve the drug effect.
Description
Technical field
The present invention relates to a kind of novel water-based pesticide preparation with double type wetting agent and preparation method thereof, and this wetting agent application in preparations such as pesticide water dispersible granules.
Background technology
Wetting agent is a kind of tensio-active agent that can make certain material inside wetted well, is widely used in agricultural chemicals, weaving, printing and dyeing, printing ink leather, washing, photograph and Polymer Synthesizing field.
Agricultural chemicals generally all is formulated by former medicine and Multiple Pesticides auxiliary agent; As process missible oil, aqua, suspension agent, wettable powder; And the desinsection soup that sprays also must adhere to fully, be bonded on the surface and polypide surface of farm crop, and stops certain hour, kill pests effectively.But; On the surface of the fine, soft fur on farm crop surfaces and polypide, one deck valuable information for systematic is all arranged, the drop that contains insecticide is difficult in and soaks on vegetation or the insect surfaces or adhere to; Thereby just do not reach the effect of desinsection; In order to give full play to drug effect, the wetting and penetrating agent that the selective wetting seepage force is strong obviously is very important.
The former medicine of most of organic syntheses is hydrophobic, need convert water and use.With water is the preparation of matrix, like wettable powder, suspension agent, water dispersible granules etc., all need add wetting agent.Mainly be aniorfic surfactant (like aliphatic alcohol sulfate, dodecylbenzene sulfonate ABS etc.) and non-ionic type (like peregal, farming breast 100 ", farming newborn 600 ", tween, sorbyl alcohol polyoxy ether etc.) at present as the wetting agent of water-base preparation.Some natural product such as sulfonated lignin, tea are withered, Chinese honey locust etc. also is wetting agent preferably.Because the effect of wetting agent can make the medicine dispersity increase, preparation stability increases, thereby helps release, infiltration and the absorption of medicine, greatly strengthens drug effect.But the Shuangzi that designs to pesticide water dispersible granules preparation structure, environment-friendly type wetting agent are not almost reported.
Summary of the invention
The objective of the invention is deficiency to prior art; The water-based pesticide preparation that a kind of green, environmental protection, efficient osmosis type are provided is with double type wetting agent and preparation method thereof; And the application of wetting agent in the environmental protection type agricultural chemical preparation that with water is external phase, raw material sources green of the present invention, environmental protection, be easy to get, the wetting agent green of preparation, environmental protection, wetting, perviousness is strong; Surface tension is low, is specially adapted to the agricultural chemicals aqueous formulation.
The objective of the invention is to realize through following technical scheme, a kind of double type wetting agent, its structural formula is:
The preparation method of described double type wetting agent is characterized in that may further comprise the steps:
(1) in reactor drum, add lipid acid and butanone, open and stir, heating makes the lipid acid dissolving; Be warmed up to 65-75 ℃, slowly drip phosphorus trichloride, in 1 hour, dropwise; Under 60-70 ℃ of constant temperature, reacted 4-6 hour then, stop to stir, the sealing static layering; Take out the upper strata stillness of night, i.e. fat acyl chloride;
(2) in reactor drum, add quadrol and butanone/triethylamine mixed solution, under agitation reaction unit is put into ice-water bath, slowly drip the fat acyl chloride that step (1) makes; Dropwise in 1 hour, reaction is after 5-7 hour, to the reaction solution suction filtration in the constant temperature ice-water bath; Get faint yellow solid; Use water washing, oven dry obtains midbody;
(3) midbody that step (2) is made adds in the reactor drum, adds the mixed solution of butanone and zero(ppm) water, stirs; Make midbody dissolving, slowly drip concentration and be 20% the 2-bromotrifluoromethane sodium sulfonate aqueous solution, uses sodium hydroxide adjusting pH value to be 8-10; Reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control, adds absolute ethanol washing, filters; Oven dry obtains the white solid powder, i.e. the double type wetting agent.
Lipid acid described in the step (1) is sfas.
Lipid acid described in the step (1) is Kui acid or coconut oil or palmitinic acid or LAURIC ACID 99 MIN, preferred LAURIC ACID 99 MIN.
Described acyl chlorides reagent is phosphorus trichloride or sulfur oxychloride, preferred phosphorus trichloride.
The mol ratio of quadrol described in the step (2) and fat acyl chloride is 2.0-2.7.
Zero(ppm) water and butanone volume ratio are 1:10-11 in the mixed solution of butanone described in the step (3) and zero(ppm) water.
The application of described double type wetting agent in the water-based pesticide preparation.
Make the reaction equation of fat acyl chloride:
Make the reaction equation of midbody:
Make the reaction equation of double type wetting agent
Double type wetting agent provided by the invention has surfactivity, compound property and wettability preferably for bisamide, disulfonate structure that long carbochain connects.The double type wetting agent is introduced carboxamido-group, helps the biological degradation of this material, reduces environmental pollution.The micella ability is strong because the singularity of its structure, double type wetting agent become, the cmc value is low; The ability that is adsorbed on the interface surpasses formation micellar ability, and it is high to reduce capillary efficient; The Krafft point is low, good water solubility, and have the excellent hydrotropy and perviousness, help formulating of recipe; Good with the compatibility of other tensio-active agents.New type double subtype wetting agent of the present invention can significantly reduce the milling time of aqua preparation, has improved working efficiency.
The synthetic mutability of the double type wetting agent molecular structure of the present invention preparation is strong, good surface activity, and wettability, seepage force are splendid, and surface tension is low, and surface tension 28.5 mN/m of 0.5mmol/L are than low 10.5 mN/m of sodium laurylsulfonate.
Synthesis technique of the present invention is simple, and reaction conditions is gentle, and is easy and simple to handle and be easy to purify, separate, the wide and environmental protection of raw material sources, and production cost is low, three-waste free pollution.
Embodiment
Below in conjunction with embodiment the present invention is done further explanation, but do not limit the present invention.Except as otherwise noted, all umbers and per-cent is all in mass in an embodiment.
Embodiment 1:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add 98g LAURIC ACID 99 MIN and 100g butanone, open and stir, under 50 ℃, make LAURIC ACID 99 MIN accomplish dissolving; Be warmed up to then about 70 ℃, slowly drip the 278g phosphorus trichloride, in 1 hour, drip off; Under 70 ℃ of constant temperature, reacted 4.5 hours then, stop stirring, the sealing static layering; Take out the upper strata stillness of night, be lauroyl chloride.
In the there-necked flask of 500ml, add butanone/triethylamine mixed solution (V:V=2:1) of 50.4g quadrol and 100ml, under agitation reaction unit is put into ice-water bath; Slowly drip lauroyl chloride 49.2g, drip in 1 hour, reaction is after 6 hours in ice-water bath; To the reaction solution suction filtration; Get faint yellow solid,, obtain midbody (amide compound) with water washing, oven dry.Reaction equation is following:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add above-mentioned midbody 63.5g; The mixed solution that adds 200ml zero(ppm) water and butanone then, wherein the volume ratio of zero(ppm) water and butanone is 1:9, stirs to make the amide compound dissolving; Slowly drip 73.85g 2-bromotrifluoromethane sodium sulfonate solution; Use sodium hydroxide to regulate pH value and be 8-10, reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control, adds absolute ethanol washing then; Filter, dry to such an extent that the white solid powder promptly gets the double type wetting agent.Double type wetting agent analysis indexes is following: (0.5% aqueous solution) surface tension 28.6mN/m; Contact angle (on the stencil plate) 9; Seepage force (canvas sedimentation) 7 seconds.
Embodiment 2:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add 98g LAURIC ACID 99 MIN and 100g butanone, open and stir, under 50 ℃, make LAURIC ACID 99 MIN accomplish dissolving; Be warmed up to then about 70 ℃, slowly drip the 278g phosphorus trichloride, in 1 hour, drip off; Under 70 ℃ of constant temperature, reacted 4.5 hours then, stop stirring, the sealing static layering; Take out the upper strata stillness of night, be lauroyl chloride.
In the there-necked flask of 500ml, add butanone/triethylamine mixed solution (V:V=2:1) of 67.2g quadrol and 100ml, under agitation reaction unit is put into ice-water bath; Slowly drip lauroyl chloride 66g, drip in 1 hour, reaction is after 6 hours in ice-water bath; To the reaction solution suction filtration; Get faint yellow solid, water washs, dries, and obtains midbody (amide compound).Reaction equation is following:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add above-mentioned midbody 64.0g; The mixed solution that adds 200ml zero(ppm) water and butanone then, wherein the volume ratio of zero(ppm) water and butanone is 1:9, stirs to make the amide compound dissolving; Slowly drip 73.9g2-bromotrifluoromethane sodium sulfonate solution; Use sodium hydroxide to regulate pH value and be 8-10, reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control, adds absolute ethanol washing then; Filter, dry to such an extent that the white solid powder promptly gets the double type wetting agent.Double type wetting agent analysis indexes is following: (0.5% aqueous solution) surface tension 27.9mN/m; Contact angle (on the stencil plate) 8; Seepage force (canvas sedimentation) 6.5 seconds.
Embodiment 3:
In the there-necked flask of the 1000ml that whisking appliance, TM, reflux condensing tube are housed, add 98g LAURIC ACID 99 MIN and 100g butanone, open and stir, under 50 ℃, make LAURIC ACID 99 MIN accomplish dissolving; Be warmed up to then about 70 ℃, slowly drip the 278g phosphorus trichloride, in 1 hour, drip off; Under 70 ℃ of constant temperature, reacted 4.5 hours then, stop stirring, the sealing static layering; Take out the upper strata stillness of night, be lauroyl chloride.
In the there-necked flask of 500ml, add butanone/triethylamine mixed solution (V:V=2:1) of 100.8g quadrol and 100ml, under agitation reaction unit is put into ice-water bath, slowly drip lauroyl chloride 98.4g; Drip in 1 hour; Reaction to the reaction solution suction filtration, got faint yellow solid after 6 hours in ice-water bath; With water washing, oven dry, obtain midbody (amide compound).Reaction equation is following:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add the mixed solution that above-mentioned midbody 64.5g adds 200ml zero(ppm) water and butanone then; Wherein the volume ratio of zero(ppm) water and butanone is 1:9; Stirring makes the amide compound dissolving, slowly drips 73.5g 2-bromotrifluoromethane sodium sulfonate solution, uses sodium hydroxide to regulate pH value and is 8-10; Reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control; Add absolute ethanol washing then, filter, dry to such an extent that the white solid powder promptly gets the double type wetting agent.Double type wetting agent analysis indexes is following: (0.5% aqueous solution) surface tension 28.4mN/m; Contact angle (on the stencil plate) 8.6; Seepage force (canvas sedimentation) 6.8 seconds.
Embodiment 4:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add 98g LAURIC ACID 99 MIN and 100g butanone, open and stir, under 50 ℃, make LAURIC ACID 99 MIN accomplish dissolving; Be warmed up to then about 70 ℃, slowly drip the 278g phosphorus trichloride, in 1 hour, drip off; Under 70 ℃ of constant temperature, reacted 4.5 hours then, stop stirring, the sealing static layering; Take out the upper strata stillness of night, be lauroyl chloride.
In the there-necked flask of 500ml, add butanone/triethylamine mixed solution (V:V=2:1) of 50.4g quadrol and 100ml, under agitation reaction unit is put into ice-water bath; Slowly drip lauroyl chloride 49.2g, drip in 1 hour, reaction is after 6 hours in ice-water bath; To the reaction solution suction filtration; Get faint yellow solid,, obtain midbody (amide compound) with water washing, oven dry.Reaction equation is following:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add above-mentioned midbody 63.8g; The mixed solution that adds 200ml zero(ppm) water and butanone then, wherein the volume ratio of zero(ppm) water and butanone is 1:9, stirs to make the amide compound dissolving; Slowly drip 2-bromotrifluoromethane sodium sulfonate 73.5g solution; Use sodium hydroxide to regulate pH value and be 8-10, reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control, adds absolute ethanol washing then; Filter, dry to such an extent that the white solid powder promptly gets the double type wetting agent.Double type wetting agent analysis indexes is following: (0.5% aqueous solution) surface tension 29.1mN/m; Contact angle (on the stencil plate) 10; Seepage force (canvas sedimentation) 8.7 seconds.
Embodiment 5:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add 98g LAURIC ACID 99 MIN and 100g butanone, open and stir, under 50 ℃, make LAURIC ACID 99 MIN accomplish dissolving; Be warmed up to then about 70 ℃, slowly drip the 278g phosphorus trichloride, in 1 hour, drip off; Under 70 ℃ of constant temperature, reacted 4.5 hours then, stop stirring, the sealing static layering; Take out the upper strata stillness of night, be lauroyl chloride.
In the there-necked flask of 500ml, add butanone/triethylamine mixed solution (V:V=2:1) of 51.2g quadrol and 100ml, under agitation reaction unit is put into ice-water bath; Slowly drip lauroyl chloride 49.2g, drip in 1 hour, reaction is after 6 hours in ice-water bath; To the reaction solution suction filtration; Get faint yellow solid,, obtain midbody (amide compound) with water washing, oven dry.Reaction equation is following:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add above-mentioned midbody 63.5g; The mixed solution that adds 200ml zero(ppm) water and butanone then, wherein the volume ratio of zero(ppm) water and butanone is 1:9, stirs to make the amide compound dissolving; Slowly drip 73.8g2-bromotrifluoromethane sodium sulfonate solution; Use sodium hydroxide to regulate pH value and be 8-10, reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control, adds absolute ethanol washing then; Filter, dry to such an extent that the white solid powder promptly gets the double type wetting agent.Double type wetting agent analysis indexes is following: (0.5% aqueous solution) surface tension 28.5mN/m; Contact angle (on the stencil plate) 8.9; Seepage force (canvas sedimentation) 7.2 seconds.
Embodiment 6:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add 98g LAURIC ACID 99 MIN and 100g butanone, open and stir, under 50 ℃, make LAURIC ACID 99 MIN accomplish dissolving; Be warmed up to then about 70 ℃, slowly drip the 278g phosphorus trichloride, in 1 hour, drip off; Under 70 ℃ of constant temperature, reacted 4.5 hours then, stop stirring, the sealing static layering; Take out the upper strata stillness of night, be lauroyl chloride.
In the there-necked flask of 500ml, add butanone/triethylamine mixed solution (V:V=2:1) of 50.4g quadrol and 100ml, under agitation reaction unit is put into ice-water bath, slowly drip lauroyl chloride 49.2g; Drip in 1 hour; Reaction to the reaction solution suction filtration, got faint yellow solid after 6 hours in ice-water bath; With water washing, oven dry, obtain midbody (amide compound).Reaction equation is following:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add above-mentioned midbody 63.6g; The mixed solution that adds 200ml zero(ppm) water and butanone then, wherein the volume ratio of zero(ppm) water and butanone is 1:9, stirs to make the amide compound dissolving; Slowly drip 73.5g2-bromotrifluoromethane sodium sulfonate solution; Use sodium hydroxide to regulate pH value and be 8-10, reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control, adds absolute ethanol washing then; Filter, dry to such an extent that the white solid powder promptly gets the double type wetting agent.Double type wetting agent analysis indexes is following: (0.5% aqueous solution) surface tension 27.8mN/m; Contact angle (on the stencil plate) 8.8; Seepage force (canvas sedimentation) 6.7.
Embodiment 7:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add 98g LAURIC ACID 99 MIN and 100g butanone, open and stir, under 50 ℃, make LAURIC ACID 99 MIN accomplish dissolving; Be warmed up to then about 70 ℃, slowly drip the 278g phosphorus trichloride, in 1 hour, drip off; Under 70 ℃ of constant temperature, reacted 4.5 hours then, stop stirring, the sealing static layering; Take out the upper strata stillness of night, be lauroyl chloride.
In the there-necked flask of 500ml, add butanone/triethylamine mixed solution (V:V=2:1) of 50.5g quadrol and 100ml, under agitation reaction unit is put into ice-water bath; Slowly drip lauroyl chloride 49.5g, drip in 1 hour, reaction is after 6 hours in ice-water bath; To the reaction solution suction filtration; Get faint yellow solid,, obtain midbody (amide compound) with water washing, oven dry.Reaction equation is following:
In the there-necked flask of the 500ml that whisking appliance, TM, reflux condensing tube are housed, add above-mentioned midbody 63.2g; The mixed solution that adds 200ml zero(ppm) water and butanone then, wherein the volume ratio of zero(ppm) water and butanone is 1:9, stirs to make the amide compound dissolving; Slowly drip 73.5g2-bromotrifluoromethane sodium sulfonate solution; Use sodium hydroxide to regulate pH value and be 8-10, reaction is 6-8 hour in 60-70 ℃ of water bath with thermostatic control, adds absolute ethanol washing then; Filter, dry to such an extent that the white solid powder promptly gets the double type wetting agent.Double type wetting agent analysis indexes is following: (0.5% aqueous solution) surface tension 28.2mN/m; Contact angle (on the stencil plate) 8.9; Seepage force (canvas sedimentation) 6.9 seconds.
Embodiment 8:
75% carbendazim water dispersing granule preparation
Component title content
Derosal (effective constituent) 75%
Dispersion agent 9%
Wetting agent (wetting agent that embodiment 1 makes) 2%
Sticker 0.6%
Disintegrating agent supplies 100%
75% derosal WDG preparation performance
Granulation performance goes out grain, and evenly the grain type is full
Wettability (time/S) 10
Slaking (time/S) 25
Suspensibility (%) 95.6
Content (%) 74.8
Heat storage stability (54 ℃, after 14 days)
Wettability (time/S) 16
Slaking (time/S) 29
Suspensibility (%) 94.8
Content (%) 74.6.
Claims (8)
1. double type wetting agent, its structural formula is:
2. the preparation method of double type wetting agent as claimed in claim 1 is characterized in that may further comprise the steps:
(1) in reactor drum, add lipid acid and butanone, open and stir, heating makes the lipid acid dissolving; Be warmed up to 65-75 ℃, slowly drip phosphorus trichloride, in 1 hour, dropwise; Under 60-70 ℃ of constant temperature, reacted 4-6 hour then, stop to stir, the sealing static layering; Take out the upper strata stillness of night, i.e. fat acyl chloride;
(2) in reactor drum, add quadrol and butanone/triethylamine mixed solution, under agitation reaction unit is put into ice-water bath, slowly drip the fat acyl chloride that step (1) makes; Dropwise in 1 hour, reaction is after 5-7 hour, to the reaction solution suction filtration in the constant temperature ice-water bath; Get faint yellow solid; Use water washing, oven dry obtains midbody;
(3) midbody that step (2) is made adds in the reactor drum, adds the mixed solution of butanone and zero(ppm) water, stirs to make the midbody dissolving; Slowly drip 30% the 2-bromotrifluoromethane sodium sulfonate aqueous solution, use sodium hydroxide to regulate pH value and be 8-10, in 60-70 ℃ of water bath with thermostatic control, reacted 6-8 hour; Add absolute ethanol washing, filter, oven dry; Obtain the white solid powder, i.e. the double type wetting agent.
3. the preparation method of double type wetting agent according to claim 2 is characterized in that the lipid acid described in the step (1) is sfas.
4. the preparation method of double type wetting agent according to claim 2 is characterized in that the lipid acid described in the step (1) is Kui acid or coconut oil or palmitinic acid or LAURIC ACID 99 MIN, preferred LAURIC ACID 99 MIN.
5. the preparation method of double type wetting agent according to claim 2 is characterized in that described acyl chlorides reagent is phosphorus trichloride or sulfur oxychloride, preferred phosphorus trichloride.
6. the preparation method of double type wetting agent according to claim 2 is characterized in that the mol ratio of quadrol described in the step (2) and fat acyl chloride is 2.0-2.7.
7. the preparation method of double type wetting agent according to claim 2 is characterized in that zero(ppm) water and butanone volume ratio are 1:10-11 in the mixed solution of butanone described in the step (3) and zero(ppm) water.
8. the application of double type wetting agent as claimed in claim 1 in the water-based pesticide preparation.
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| CN201110102268A CN102311368A (en) | 2011-04-22 | 2011-04-22 | Twin-type wetting agent as well as preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105707071A (en) * | 2016-01-21 | 2016-06-29 | 威尔（福建）生物有限公司 | Wetting agent for pesticide preparations, method for preparing wetting agent and application of wetting agent to pesticide preparations |
| CN111559970A (en) * | 2020-05-28 | 2020-08-21 | 陕西科技大学 | Surface wetting agent with polysulfonic acid structure and preparation method thereof |
| CN111635747A (en) * | 2020-06-05 | 2020-09-08 | 赛科思能源技术(重庆)有限责任公司 | Imbibition displacement agent for developing compact oil |
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| CN101659634A (en) * | 2009-09-09 | 2010-03-03 | 中国海洋石油总公司 | Synthetic method of anion sulfoacid gemini surfactant DTM |
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| CN101659634A (en) * | 2009-09-09 | 2010-03-03 | 中国海洋石油总公司 | Synthetic method of anion sulfoacid gemini surfactant DTM |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105707071A (en) * | 2016-01-21 | 2016-06-29 | 威尔（福建）生物有限公司 | Wetting agent for pesticide preparations, method for preparing wetting agent and application of wetting agent to pesticide preparations |
| CN111559970A (en) * | 2020-05-28 | 2020-08-21 | 陕西科技大学 | Surface wetting agent with polysulfonic acid structure and preparation method thereof |
| CN111635747A (en) * | 2020-06-05 | 2020-09-08 | 赛科思能源技术(重庆)有限责任公司 | Imbibition displacement agent for developing compact oil |
| CN111635747B (en) * | 2020-06-05 | 2023-03-31 | 赛科思能源技术(重庆)有限责任公司 | Imbibition displacement agent for developing compact oil |
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