CN107469414B - One kind defoaming agent containing poly-organosilicon and preparation method thereof - Google Patents
One kind defoaming agent containing poly-organosilicon and preparation method thereof Download PDFInfo
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- CN107469414B CN107469414B CN201710935231.5A CN201710935231A CN107469414B CN 107469414 B CN107469414 B CN 107469414B CN 201710935231 A CN201710935231 A CN 201710935231A CN 107469414 B CN107469414 B CN 107469414B
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- organic silicon
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0409—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing Si-atoms
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0427—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing halogen-atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
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- Medicinal Chemistry (AREA)
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- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Degasification And Air Bubble Elimination (AREA)
Abstract
The invention discloses a kind of organic silicon defoamers and preparation method thereof containing the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-, the raw material of the organic silicon defoamer forms percentage are as follows: the trapezoidal fluorohydrocarbon base silsesquioxane copolymer 10~30% of dimethyl silicone polymer-, dimethicone 10~30%, hydrophobic silicic aerogels 4~8%, emulsifier 5~10%, thickener 0.1~0.3%, deionized water 50~70%.Organic silicon defoamer defoaming of the invention is rapid, foam inhibition is lasting, emulsion-stabilizing, and shrinkage cavity will not be caused on the substrates such as PVC film, is had a wide range of application.The preparation process of the organic silicon defoamer is simple, and production cost is low, and product is excellent for the defoaming effect of emulsion polymerization especially polyaminoester emulsion polymerization reaction.
Description
Technical field
The invention belongs to organosilicon auxiliary agent technical fields, in particular to a kind of to contain the trapezoidal fluorohydrocarbon of dimethyl silicone polymer-
The organic silicon defoamer and preparation method thereof of base silsesquioxane copolymer.
Background technique
Methyl-silicone oil as defoaming agent have low surface tension, low aqueous solubility, high activity, low volatility, chemical inertness,
The characteristics such as physiological-toxicity-free, antifoaming speed is fast, the foam inhibition time is long, widely applicable, but heat-resisting quantity is poor, and strong basicity resisting is weak；And ether
Class defoaming agent, although spreading coefficient is big, good water solubility, high temperature resistant, resistance to highly basic, antifoaming speed and foam inhibition time all less managed
Think.In recent years, ether modified siloxane becomes the hot spot researched and developed both at home and abroad.It is grafted by ether or block modified, plays two kinds of groups
The synergisticing performance divided.Hydrophilic ether segment assigns self-emulsifying.Hydrophobic siloxanes segment assigns its low surface tension, no
Defoaming and suds suppressing properties are improved only, its excellent heat resistance, acid and alkali-resistance, anti-aging, electrical isolation, flexibility, nontoxic is also assigned
Tasteless, stable storing and it is easy to use the advantages that.
Emulsion-type organic silicon defoamer is generally by dimethicone, hydrophobic silicic aerogels, emulsifier, thickener and deionized water
Etc. compounding.Effective component dimethicone is in soft linear structure, in the system containing exhibiting high surface activating agent very
It is easy to be solubilized, lose defoaming and foam inhibition effect.
Patent CN201611211752.8 describes a kind of preparation method of silicone antifoaming agent, wherein poly- methyl times
Half siloxane micro powder compounds with ingredients such as modified silicon oil and white carbon blacks and emulsion type defoaming agent is made.Patent CN201710265261.X
A kind of defoaming agent and preparation method thereof of fluorine richness silicone oil is described, wherein linear fluorine richness siloxanes and white carbon black, coupling agent
Etc. compoundings emulsion type defoaming agent is made.The trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl polysiloxane-is for water-based emulsion
In organosilicon auxiliary agent solubility parameters difference it is big, with its for main active princlple defoaming agent up to the present, be also little affected by
Concern.
The present invention provides a kind of organosilicon containing the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-and disappears
Infusion.Defoaming agent defoaming of the invention is rapider, and foam inhibition is more longlasting, and dilution stability more preferably, does not cause to contract on PVC base surface
Hole has a wide range of application.
Summary of the invention
The purpose of the present invention is to provide one kind to contain the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-
Organic silicon defoamer and preparation method thereof, keep antifoam composition not solubilized in the system containing exhibiting high surface activating agent, it is long
Kubo holds good defoaming and foam inhibition effect, while having more preferably dilution stability.
A kind of organic silicon defoamer containing the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-, raw material
Composition percentage by weight is calculated as:
300~2000cSt of the dimethyl-silicon oil viscosity；
The general structure of the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-is as follows:
M is the integer in 5-20, and n is the integer in 5-20；
The trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-the preparation method is as follows:
The ethanol solution of the toluene solution of hydroxy silicon oil and ten difluoro heptyl propyl trimethoxy silicanes is added to be equipped with and is stirred
In the three-necked flask for mixing paddle, reflux condensing tube and thermometer, stirring to it is pure it is transparent after, with NaOH or KOH saturated solution tune
PH12~14,60~80 DEG C of 6~7h of reaction.Then toluene, ethyl alcohol, unreacted ten difluoros heptan are evaporated under reduced pressure out for 130~150 DEG C
Base propyl trimethoxy silicane and by-product etc. obtain the trapezoidal fluorohydrocarbon base silsesquioxane polymer of dimethyl silicone polymer-；
The synthetic reaction equation of the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-is as follows:
M is the integer in 5-20, and n is the integer in 5-20.
The trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-is main antifoam composition of the invention, is in
Three-dimensional structure increases toughness and intensity than linear silicone oils, and general surfactant is difficult to emulsify, will not be solubilized；
The fluorohydrocarbon base contained be capable of sending down abnormally ascending bubble surface can, be adsorbed onto the siloxanes of low surface tension on vacuolar membrane rapidly, and film it
Between build bridge draining, rupture film.Thus the trapezoidal fluorohydrocarbon base silsesquioxane polymer of dimethyl silicone polymer-can keep for a long time good
Good defoaming and foam inhibition effect；Simultaneously the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-be oily liquids and
It is not powdery solid, dilution stability more preferably, does not cause shrinkage cavity, and application range is wider.
The molar ratio of the hydroxy silicon oil and ten difluoro heptyl propyl trimethoxy silicanes is 1:(1.1~1.5)；
The ethanol solution concentration of the toluene solution of the hydroxy silicon oil and ten difluoro heptyl propyl trimethoxy silicanes is
30~80%.
The hydroxy silicon oil is end hydroxyl silicone oil, and hydroxy radical content is 3~30%；
The hydrophobic silicic aerogels are that the specific surface area handled through hexamethyldisilazane is 200~300m2The gas phase of/g is white
Carbon black.
The emulsifier is Siloxane-Oxyalkylene Copolymers nonionic surfactant.
The thickener is sodium acrylate.
The preparation of the above-mentioned organic silicon defoamer containing the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-
Method, comprising the following steps:
(1) by dimethicone, the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-and hydrophobic silicic aerogels
It is mixed in double planetary mixer；
(2) by step (1) gains with high speed shear dispersion machine with 1000~2000r/min, stir 30min；
(3) emulsifier is added in step (2) gains, then proceedes to stirring 30min, while deionized water and increasing is added dropwise
Thick dose of aqueous solution is further continued for stirring 30-60min.
The invention has the benefit that
The present invention contains the organic silicon defoamer defoaming of the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-
Rapidly, foam inhibition persistently, emulsion-stabilizing, do not cause shrinkage cavity.The preparation method simple process of organic silicon defoamer of the present invention, without adding
Heat significantly reduces production cost, and for product for emulsion polymerization, the defoaming effect of especially polyaminoester emulsion polymerization reaction is excellent
It is different, technical support is provided for industry energy conservation emission reduction.
Detailed description of the invention
Fig. 1 is the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-prepared by the present invention1H-NMR figure
Spectrum.
Specific embodiment
The present invention provides a kind of organosilicons containing the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-
Defoaming agent and preparation method thereof.Below with reference to embodiment, the present invention is described in more detail.
Embodiment 1
The hydroxy silicon oil 100g of 100g/mol is dissolved in 50g toluene, ten difluoro heptyl propyl trimethoxy silicane 585g
It is dissolved in 200g ethyl alcohol, sequentially adds in the 2000mL three-necked flask equipped with agitating paddle, reflux condensing tube and thermometer, stir
To it is pure it is transparent after, with NaOH saturated solution adjust pH=12,80 DEG C of reaction 6h.Then 150 DEG C of vacuum distillations, obtain poly- diformazan
The trapezoidal fluorohydrocarbon base silsesquioxane copolymer of radical siloxane-；
By dimethicone 200g, the trapezoidal fluorohydrocarbon base silsesquioxane copolymer 200g of dimethyl silicone polymer-, hydrophobic white
Carbon black 40g is mediated in double planetary mixer, then stirs 30min with dispersion machine 1000r/min, and emulsifier 50g, 1000r/ is added
Min stirs 30min, and 400g deionized water 30min is added dropwise, then 1% thickening made of thickener 1g and deionized water 100g is added dropwise
Agent aqueous solution, 1000r/min stir 30min, are made described total containing the trapezoidal fluorohydrocarbon base silsesquioxane of dimethyl silicone polymer-
The organic silicon defoamer of polymers.
Embodiment 2
300g/mol hydroxy silicon oil 150g is dissolved in 100g toluene, ten difluoro heptyl propyl trimethoxy silicane 320g are molten
It in 100g ethyl alcohol, sequentially adds in the 2000mL three-necked flask equipped with agitating paddle, reflux condensing tube and thermometer, stirring is extremely
It is pure it is transparent after, with KOH saturated solution adjust pH=13,70 DEG C of reaction 7h.Then 140 DEG C of vacuum distillations, obtain poly dimethyl
The trapezoidal fluorohydrocarbon base silsesquioxane polymer of siloxanes-；
By dimethicone 300g, the trapezoidal fluorohydrocarbon base silsesquioxane copolymer 100g of dimethyl silicone polymer-, hydrophobic white
Carbon black 50g is mediated in double planetary mixer, then stirs 30min with dispersion machine 1000r/min, and emulsifier 60g, 1500r/ is added
Min stirs 30min, and 400g deionized water 30min is added dropwise, then 1% increasing made of thickener 1.5g and deionized water 150g is added dropwise
Thick dose of aqueous solution, 1500r/min stir 30min, are made described and contain the trapezoidal fluorohydrocarbon base silsesquioxane of dimethyl silicone polymer-
The organic silicon defoamer of copolymer.
Embodiment 3
600g/mol hydroxy silicon oil 200g is dissolved in 100g toluene, ten difluoro heptyl propyl trimethoxy silicane 231g are molten
It in 100g ethyl alcohol, sequentially adds in the 2000mL three-necked flask equipped with agitating paddle, reflux condensing tube and thermometer, stirring is extremely
It is pure it is transparent after, with NaOH saturated solution adjust pH=14,60 DEG C of reaction 6.5h.Then 130 DEG C of vacuum distillations, obtain poly- diformazan
The trapezoidal fluorohydrocarbon base silsesquioxane polymer of radical siloxane-；
By dimethicone 100g, the trapezoidal fluorohydrocarbon base silsesquioxane copolymer 300g of dimethyl silicone polymer-, hydrophobic white
Carbon black 60g is mediated in double planetary mixer, then stirs 30min with dispersion machine 1500r/min, and emulsifier 80g, 2000r/ is added
Min stirs 30min, and 400g deionized water 30min is added dropwise, then 1% thickening made of thickener 2g and deionized water 200g is added dropwise
Agent aqueous solution, 2000r/min stir 30min, are made described total containing the trapezoidal fluorohydrocarbon base silsesquioxane of dimethyl silicone polymer-
The organic silicon defoamer of polymers.
Embodiment 4
1000g/mol hydroxy silicon oil 200g is dissolved in 100g toluene, ten difluoro heptyl propyl trimethoxy silicane 158g
It is dissolved in 50g ethyl alcohol, sequentially adds in the 1000mL three-necked flask equipped with agitating paddle, reflux condensing tube and thermometer, stir
To it is pure it is transparent after, with KOH saturated solution adjust pH=13,60 DEG C of reaction 6.5h.Then 130 DEG C of vacuum distillations, obtain poly- two
The trapezoidal fluorohydrocarbon base silsesquioxane polymer of methylsiloxane-；
By dimethicone 250g, the trapezoidal fluorohydrocarbon base silsesquioxane copolymer 150g of dimethyl silicone polymer-, hydrophobic white
Carbon black 80g is mediated in double planetary mixer, then stirs 30min with dispersion machine 2000r/min, and emulsifier 100g is added,
2000r/min stirs 30min, 400g deionized water 30min is added dropwise, then be added dropwise made of thickener 3g and deionized water 300g
1% aqueous thickener solution, 2000r/min stir 30min, are made described and contain the trapezoidal fluorohydrocarbon base sesquialter of dimethyl silicone polymer-
The organic silicon defoamer of silicone copolymers.
Embodiment 5
Organosilicon defoaming prepared by the present invention containing the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-
Defoaming effect of the agent when polyaminoester emulsion is processed is as follows, and defoaming agent additional amount is the 0.25% of polyaminoester emulsion weight, system
Foam time and yield rate are counted, the result is as follows:
| Defoaming agent type | Foam time/min | Yield rate/% |
| Embodiment 1 | 5 | 99.99 |
| Embodiment 2 | 8 | 99.92 |
| Embodiment 3 | 10 | 99.87 |
| Embodiment 4 | 9 | 99.89 |
| Commercially available silicon oil foam killer | 40 | 94.86 |
| Commercially available modified silicon oil defoaming agent | 30 | 95.68 |
As seen from the above table, defoaming agent defoaming effect provided by the invention is substantially better than common defoaming agent, and can mention
Rise the yield rate of polyaminoester emulsion product.
Technical solution of the present invention is described in detail in above-described embodiment.It is apparent that the present invention is not limited being retouched
The embodiment stated.Based on the embodiments of the present invention, those skilled in the art can also make a variety of variations accordingly, but appoint
What is equal with the present invention or similar variation shall fall within the protection scope of the present invention.
Claims (8)
1. a kind of organic silicon defoamer, which is characterized in that raw material forms percentage are as follows:
The general structure of the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-is as follows:
M is the integer in 5-20, and n is the integer in 0-20；
The trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-the preparation method is as follows:
By the ethanol solution of the toluene solution of hydroxy silicon oil and ten difluoro heptyl propyl trimethoxy silicanes be added equipped with agitating paddle,
In the three-necked flask of reflux condensing tube and thermometer, stirring to it is pure it is transparent after, adjust reaction system with NaOH or KOH solution
PH=12~14,60~80 DEG C of 6~7h of reaction；Then dilute hydrochloric acid is added and is neutralized to pH=7, is evaporated under reduced pressure out solvent toluene, anti-
Ethyl alcohol, unreacted monomer and the by-product that should be generated obtain the trapezoidal fluorohydrocarbon base silsesquioxane copolymerization of dimethyl silicone polymer-
Object.
2. organic silicon defoamer according to claim 1, which is characterized in that the trapezoidal fluorohydrocarbon of dimethyl silicone polymer-
The synthetic reaction equation of base silsesquioxane copolymer is as follows:
Wherein, m is the integer in 5-20, and n is the integer in 0-20.
3. organic silicon defoamer according to claim 1, which is characterized in that the hydroxy silicon oil and ten difluoro heptyl propyl
The molar ratio of trimethoxy silane is 1:(1.1~1.5).
4. organic silicon defoamer according to claim 1, which is characterized in that the hydroxy silicon oil is end hydroxyl silicone oil, hydroxyl
Base content is 3~30%.
5. organic silicon defoamer according to claim 1, which is characterized in that the dimethyl-silicon oil viscosity be 300~
2000cSt。
6. organic silicon defoamer according to claim 1, which is characterized in that the hydrophobic silicic aerogels are through two silicon of hexamethyl
The specific surface area of azane processing is 200~300m2The gas-phase silica of/g.
7. organic silicon defoamer according to claim 1, which is characterized in that the emulsifier is Siloxane-Oxyalkylene Copolymers
Nonionic surfactant, the thickener are sodium acrylate.
8. the preparation method of any one of the claim 1-7 organic silicon defoamer, which comprises the following steps:
(1) by dimethicone, the trapezoidal fluorohydrocarbon base silsesquioxane copolymer of dimethyl silicone polymer-and hydrophobic silicic aerogels double
It is mixed in planetary mixer；
(2) by step (1) gains with high speed shear dispersion machine with 1000~2000r/min, stir 30min；
(3) emulsifier is added in step (2) gains, then proceedes to stirring 30min, while deionized water and thickener is added dropwise
Aqueous solution is further continued for stirring 30-60min.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108721949A (en) * | 2018-05-25 | 2018-11-02 | 高阳 | A kind of organic silicon defoamer and preparation method thereof |
| CN109966786B (en) * | 2019-03-14 | 2021-06-11 | 中天东方氟硅材料有限公司 | Organic silicon defoaming agent of trifluoropropene modified organic silicon high-boiling residues |
| CN112263851A (en) * | 2020-09-30 | 2021-01-26 | 四川健能制药有限公司 | Preparation method of simethicone defoaming composition |
| CN114316610B (en) * | 2021-12-13 | 2023-05-23 | 南京瑞思化学技术有限公司 | Preparation method of organic silicon emulsion |
| CN115300947A (en) * | 2022-08-22 | 2022-11-08 | 山东师范大学实验厂有限公司 | Efficient defoaming agent for pesticide and preparation method thereof |
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| GB1251170A (en) * | 1967-12-06 | 1971-10-27 | Stauffer Chemical Co | |
| CN1641097A (en) * | 2004-12-10 | 2005-07-20 | 曹治平 | Moderate temperature prnited and dyed organosilicon anti-bubbling and its preparing method |
| CN1931417A (en) * | 2006-07-28 | 2007-03-21 | 南京四新科技应用研究所有限公司 | Prepn process of active defoaming agent composition |
| CN101875667A (en) * | 2009-11-20 | 2010-11-03 | 河海大学 | Dodecafluoroheptyl-propyl polyhedral oligomeric silsesquioxane and preparation method thereof |
| CN104722102A (en) * | 2015-03-01 | 2015-06-24 | 江门职业技术学院 | Preparation method of high-efficiency polyether organic silicon defoaming agent applied under severe environment |
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2017
- 2017-10-10 CN CN201710935231.5A patent/CN107469414B/en active Active
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|---|---|---|---|---|
| GB1251170A (en) * | 1967-12-06 | 1971-10-27 | Stauffer Chemical Co | |
| CN1641097A (en) * | 2004-12-10 | 2005-07-20 | 曹治平 | Moderate temperature prnited and dyed organosilicon anti-bubbling and its preparing method |
| CN1931417A (en) * | 2006-07-28 | 2007-03-21 | 南京四新科技应用研究所有限公司 | Prepn process of active defoaming agent composition |
| CN101875667A (en) * | 2009-11-20 | 2010-11-03 | 河海大学 | Dodecafluoroheptyl-propyl polyhedral oligomeric silsesquioxane and preparation method thereof |
| CN104722102A (en) * | 2015-03-01 | 2015-06-24 | 江门职业技术学院 | Preparation method of high-efficiency polyether organic silicon defoaming agent applied under severe environment |
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