CN101376089A - Method for preparing foam killer - Google Patents
Method for preparing foam killer Download PDFInfo
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- CN101376089A CN101376089A CNA2008101214676A CN200810121467A CN101376089A CN 101376089 A CN101376089 A CN 101376089A CN A2008101214676 A CNA2008101214676 A CN A2008101214676A CN 200810121467 A CN200810121467 A CN 200810121467A CN 101376089 A CN101376089 A CN 101376089A
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- polyglycerol
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- polymerization
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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
Abstract
The invention discloses a preparation method of a deformer. The method comprises the following steps: polymerizing glycerin into polyglycerol with the average polymerization degree of 2 to 15 under the effect of a catalyst; carrying out ring opening polymerizing reaction among polyglycerol, propylene oxide and epoxy ethane to get polyglycerol polyalkoxy ether; and conducting esterification reaction between polyglycerol polyalkoxy ether and C12 to C22 fatty acid to get the deformer. The preparation method is easy to operate and has low cost; and the deformer produced by using the method has excellent deforming effect and can be widely applied into use.
Description
Technical field
The present invention relates to the industrial defoaming agent field, be specifically related to a kind of preparation method of defoamer.
Background technology
In industrial processes, as food fermentation, bio-pharmaceuticals, papermaking, textile sizing, petrochemical industry, industrial cleaning, coating, latex etc., all can produce many foams, need froth breaking fast and effeciently.Adding defoamer is the most frequently used method, and the kind of defoamer is a lot, as natural oil lipid, long carbochain alcohols, long carbochain amide-type, polyethers, defoamer such as polysiloxane-based.
The natural oil defoamer can directly extract from natural products as rape oil, soya-bean oil, corn wet goods, and is cheap and easy to get; But the natural oil defoamer is insoluble in water, only the liquid surface foam is had the froth breaking effect, can not drive, eliminate the foam that is scattered in liquid internal, and the not anti-storage of natural oil, easily become sour rottenly, influences antifoam performance.
By polyglycerol is introduced natural oil, can effectively improve the hydrophily of this defoamer, as: U.S. Pat 5429718 discloses a kind of polyglycerol defoamer, the degree of polymerization of glycerine is 3～6, esterification degree is 15～85%, can be used for the slurrying of paper industry, the operation of copying generation foams such as paper, plain boiled water circulation, pigment dispersion, coating coating, do not need the composite of auxiliary defoamer.Chinese patent CN1721031 discloses a kind of industrial defoaming agent, glycerine is aggregated into the degree of polymerization under the catalyst condition be 2～10 polymerization glycerine, mass ratio adding fatty acid glyceride or aliphatic acid carry out ester exchange in accordance with regulations then, obtain defoamer, can be used for technologies such as papermaking, sugaring, fermentation.Because the viscosity very big (particularly the degree of polymerization was above 6 o'clock) of polyglycerol has a strong impact on the use of defoamer; Because the hydrophilic radical of polyglycerol defoamer is closely wrapped up by a plurality of lipophilic groups, being difficult to influences antifoam performance in the aqueous phase diffusion in addition.
Summary of the invention
The invention provides a kind of preparation method of defoamer, prepared defoamer has good froth breaking effect, applied range, and the preparation method is simple, and cost is low.
A kind of preparation method of defoamer comprises:
(1) catalyst dissolution is mixed with glycerine behind water, reacts 0.5～2 hour down at 110～200 ℃, removes the free water in the reaction system; Reacted 2.5～4.5 hours down at 235～280 ℃, remove the water that reaction generates, the average degree of polymerization that obtains degree of polymerization distribution comparison homogeneous is 2～15 polyglycerol, and preferred average degree of polymerization is 3～8 polyglycerol;
(2) in the product that step (1) obtains, add expoxy propane, oxirane, under the catalyst identical, ring-opening polymerization takes place, obtain the poly-alkoxyl ether of polyglycerol at 80～140 ℃ with step (1); Wherein the mass ratio of polyglycerol, expoxy propane and oxirane is 1:0～50:0～25, and the amount of expoxy propane, oxirane is not zero simultaneously; Control the polymerization order by expoxy propane, oxirane monomers charging sequence, make that the polymerisation of polyglycerol and expoxy propane, oxirane can be the block or the atactic polymerization of random order; Residual catalyst reacts in the product that ring-opening polymerization also can be directly obtains by step (1); Wherein but catalyst consumption is the amount of catalysis ring-opening polymerization, generally is no more than 5/1000ths of the poly-alkoxyl ether total amount of polyglycerol.
(3) with poly-alkoxyl ether of the polyglycerol of step (2) preparation and C
12～C
22Aliphatic acid carries out esterification and obtains defoamer under esterification catalyst catalysis; Poly-alkoxyl ether of polyglycerol and C
12～C
22The mass ratio of aliphatic acid is 30%～100% to adjust by the esterification degree of the poly-alkoxyl ether of polyglycerol; Esterification degree is meant that the hydroxyl value of esterification and the ratio of total hydroxyl value take advantage of 100%.
Described catalyst is one or both in potassium hydroxide, the NaOH.
Described esterification catalyst is conventional esterification catalyst, a kind of in preferred p-methyl benzenesulfonic acid, sulfuric acid, the solid acid.
Described C
12～C
22Aliphatic acid can be one or more in straight chain, side chain, saturated, the unrighted acid arbitrarily.
The present invention has following advantage:
The present invention is initiator with the polyglycerol, in the presence of catalyst, cause the polymerization of expoxy propane, oxirane, obtain the poly-alkoxyl ether of polyglycerol, terminal hydroxy group to the poly-alkoxyl ether of polyglycerol carries out esterification then, obtain defoamer, the preparation method of this defoamer is simple, does not need to handle residue.
Compare with the polyglycerol fatty acid ester, the poly-alkoxyl ether fatty acid ester defoamer of the polyglycerol of the present invention's preparation, longer hydrophilic chain link, longer oleophylic chain link are arranged in its molecule, viscosity is low, helping defoamer disperses at aqueous phase, also help on the liquid film of foam, adsorbing, improved the efficient of froth breaking; Simultaneously by changing the amount and the esterification degree of expoxy propane, oxirane, can regulate hydrophilic hydrophobic balance value (being the HLB value), the molecular weight of defoamer easily, the scope of application of defoamer is increased, be applicable to that nearly all needs carry out the production technology of froth breaking.
The specific embodiment
Embodiment 1
In the voltage-resistant reactor of a belt stirrer, thermometer, condenser, add 184 gram glycerine (2mol), 6.84 gram potassium hydroxide aqueous solution (wherein potassium hydroxide 1.84 grams) heats to 160 ℃, stirring reaction distilled out about 5.5 gram water from condenser after 1 hour; Continue to be warmed up to 250 ℃, stirring reaction went out about 24 gram water from the condenser redistillation after 3 hours, obtained polyglycerol; Calculate that from the water yield that distills out that adds for the second time thermal response this moment, the average degree of polymerization of polyglycerol was about 3.
The product that obtains is cooled to 120 ℃, adds 5610 gram expoxy propane successively, 2200 gram oxirane carry out ring-opening polymerization, reaction finishes after neutralization, decolouring obtain polyglycerol polyoxyethylene polyoxypropylene ether, and its hydroxyl value is 25mgKOH/g.
Get above-mentioned polyglycerol polyoxyethylene polyoxypropylene ether 500 grams, add oleic acid 62.8 grams, add catalyst sulfuric acid (mass concentration is 98%) 5 grams, be heated to 175 ℃ of reactions and obtained polyglycerol polyoxyethylene polyoxypropylene oleic acid ester defoamer in 8 hours, its esterification degree is 100%.
Embodiment 2
In the voltage-resistant reactor of a belt stirrer, thermometer, condenser, add 184 gram glycerine (2mol), 6.84 gram potassium hydroxide aqueous solution (wherein potassium hydroxide 1.84 grams) heats to 200 ℃, stirring reaction distilled out about 5.5 gram water from condenser after 1 hour; Continue to be warmed up to 265 ℃, go out about 30 gram water from the condenser redistillation after 4 hours, obtain polyglycerol; The water yield that distills out that adds thermal response from second step calculates that this moment, the average degree of polymerization of polyglycerol was about 6.
The product that obtains is cooled to 120 ℃, and adding 2800 gram expoxy propane carry out ring-opening polymerization, react end after neutralize, decolour, and obtain the polyglycerol polyethenoxy ether, and its hydroxyl value is 53mgKOH/g.
Get above-mentioned polyglycerol polyethenoxy ether 500 grams, add palmitic acid 36.8 grams, add catalyst p-methyl benzenesulfonic acid 3.9 grams, be heated to 150 ℃ of reactions and obtained polyglycerol polyethenoxy ether palmitate defoamer in 11 hours, its esterification degree is 50%.
Embodiment 3
In the voltage-resistant reactor of a belt stirrer, thermometer, condenser, add 184 gram glycerine (2mol), 6.78 gram potassium hydroxide aqueous solution (wherein potassium hydroxide 1.78 grams) heats to 180 ℃, stirring reaction distilled out about 5.5 gram water from condenser after 1.5 hours; Continue to be warmed up to 235 ℃, stirring reaction went out about 24 gram water from the condenser redistillation after 4.5 hours; The water yield that distills out that adds thermal response from second step calculates that this moment, the average degree of polymerization of polyglycerol was about 3.
The product that obtains is cooled to 120 ℃, adds 2200 gram oxirane successively, 1120 gram expoxy propane carry out ring-opening polymerization, reaction finishes after neutralization, decolouring obtain the polyglycerol polyoxyethylene poly-oxygen propylene aether, and its hydroxyl value is 55mgKOH/g.
Get above-mentioned polyglycerol polyoxyethylene poly-oxygen propylene aether 500 grams, add stearic acid 40.6 grams, add catalyst sulfuric acid (mass concentration is 98%) 5 grams, be heated to 160 ℃ of reactions and obtained polyglycerol polyoxyethylene poly-oxygen propylene aether stearate defoamer in 7 hours, its esterification degree is 30%.
Embodiment 4
In the voltage-resistant reactor of a belt stirrer, thermometer, condenser, add 184 gram glycerine (2mol), 7 gram sodium hydrate aqueous solutions (wherein NaOH 2 grams) heat to 190 ℃, and stirring reaction distilled out about 5.7 gram water from condenser after 1.5 hours; Continue to be warmed up to 280 ℃, stirring reaction went out about 34 gram water from the condenser redistillation after 4 hours, obtained polyglycerol; Calculate that from the water yield that distills out that adds for the second time thermal response this moment, the average degree of polymerization of polyglycerol was about 11.
The product that obtains is cooled to 80 ℃, and adding 3500 restrains oxirane, 5 gram NaOH carry out ring-opening polymerization, reacts end after neutralize, decolour, and obtains the polyglycerol APEO, and its hydroxyl value is 38mgKOH/g.
Get poly-alkoxyl ether 500 grams of above-mentioned polyglycerol, add vegetable oil acid 95.5 grams, add catalyst p-methyl benzenesulfonic acid 4.2 grams, be heated to 175 ℃ of reactions 8.5 hours, obtain polyglycerol polyoxyethylene oleic acid ester defoamer, its esterification degree is 100%.
Embodiment 5
In the voltage-resistant reactor of a belt stirrer, thermometer, condenser, add 184 gram glycerine (2mol), the aqueous solution of 8 gram NaOH and potassium hydroxide mixture (wherein NaOH 1 gram and potassium hydroxide 1.5 grams), heat to 200 ℃, stirring reaction distilled out about 5.5 gram water from condenser after 1.4 hours; Continue to be warmed up to 275 ℃, stirring reaction went out about 36.2 gram water from the condenser redistillation after 4.5 hours, obtained polyglycerol; Calculate that from the water yield that distills out that adds for the second time thermal response this moment, the average degree of polymerization of polyglycerol was about 15.
The product that obtains is cooled to 80 ℃, adds 1720 gram expoxy propane successively, 517 gram oxirane carry out ring-opening polymerization, reaction finishes after neutralization, decolouring obtain polyglycerol polyoxyethylene polyoxypropylene ether, and its hydroxyl value is 49mgKOH/g.
Get above-mentioned polyglycerol polyoxyethylene polyoxypropylene ether 500 grams, add erucic acid 118 grams, add catalyst p-methyl benzenesulfonic acid 3.5 grams, phosphorous acid 1.8 grams, be heated to 166 ℃ of reactions 10 hours, obtain polyglycerol polyoxyethylene polyoxypropylene ether eruciate defoamer, its esterification degree is 80%.
Embodiment 6
In the voltage-resistant reactor of a belt stirrer, thermometer, condenser, add 184 gram glycerine (2mol), 7.4 (wherein NaOH 0.4 gram and potassium hydroxide 0.6 restrain the aqueous solution of gram NaOH and potassium hydroxide mixture, heat to 120 ℃, stirring reaction distilled out about 6.5 gram water from condenser after 1 hour; Continue to be warmed up to 240 ℃, stirring reaction went out about 27 gram water from the condenser redistillation after 4.5 hours, obtained polyglycerol; Calculate that from the water yield that distills out that adds for the second time thermal response this moment, the average degree of polymerization of polyglycerol was about 4.
The product that obtains is cooled to 95 ℃, adds 2200 gram expoxy propane successively, 400 gram oxirane carry out ring-opening polymerization, reaction finishes after neutralization, decolouring obtain polyglycerol polyoxyethylene polyoxypropylene ether, and its hydroxyl value is 51mgKOH/g.
Get above-mentioned polyglycerol polyoxyethylene polyoxypropylene ether 500 grams, add laurate 90 grams, add catalyst p-methyl benzenesulfonic acid 2.4 grams, be heated to 185 ℃ of reactions and obtained polyglycerol polyoxyethylene polyoxypropylene ether laurate defoamer in 8.5 hours, its esterification degree is 96%.
Embodiment 7
In the voltage-resistant reactor of a belt stirrer, thermometer, condenser, add 184 gram glycerine (2mol), 6.84 gram potassium hydroxide aqueous solution (wherein potassium hydroxide 1.84 grams) heats to 200 ℃, stirring reaction distilled out about 5.5 gram water from condenser after 1 hour; Continue to be warmed up to 265 ℃, go out about 30 gram water from the condenser redistillation after 4 hours, obtain polyglycerol; The water yield that distills out that adds thermal response from second step calculates that this moment, the average degree of polymerization of polyglycerol was about 6.
The product that obtains is cooled to 120 ℃, and adding 2800 gram expoxy propane carry out ring-opening polymerization, react end after neutralize, decolour, and obtain the polyglycerol polyethenoxy ether, and its hydroxyl value is 53mgKOH/g.
Get above-mentioned polyglycerol polyethenoxy ether 500 grams, add palmitic acid 18 grams, oleic acid 18.8 grams, add catalyst p-methyl benzenesulfonic acid 3.9 grams, be heated to 150 ℃ of reactions and obtained polyglycerol polyethenoxy ether palmitate defoamer in 11 hours, its esterification degree is 50%.
The defoaming effect test:
Test method: in a 2500ml graduated cylinder that high speed agitator is housed, add 1000ml foaming medium and a certain amount of defoamer, start to stir also and pick up counting writing time when foam height reaches 500ml, 1000ml, 1500ml.Under the same terms, the time is long more, and the expression defoaming effect is good more.Result of the test such as following table (percentage is mass percent in the table):
Claims (6)
1, a kind of preparation method of defoamer comprises the steps:
(1) catalyst dissolution is mixed with glycerine behind water, 110～200 ℃ of down reactions 0.5～2 hour, again 235～280 ℃ of reactions 2.5～4.5 hours down, obtains average degree of polymerization and be 2～15 polyglycerol;
(2) in the product that step (1) obtains, add expoxy propane, oxirane, under the catalyst identical, carry out ring-opening polymerization, obtain the poly-alkoxyl ether of polyglycerol at 80～140 ℃ with step (1); Wherein the mass ratio of polyglycerol, expoxy propane and oxirane is 1:0～50:0～25, and the amount of expoxy propane, oxirane is not zero simultaneously;
(3) with poly-alkoxyl ether of the polyglycerol of step (2) preparation and C
12～C
22Aliphatic acid carries out esterification and obtains defoamer under esterification catalyst catalysis; Poly-alkoxyl ether of polyglycerol and C
12～C
22The mass ratio of aliphatic acid is 30%～100% to adjust by the esterification degree of the poly-alkoxyl ether of polyglycerol.
2, preparation method as claimed in claim 1 is characterized in that: described polyglycerol average degree of polymerization is 3～8.
3, preparation method as claimed in claim 1 is characterized in that: described catalyst is the mixture of potassium hydroxide or NaOH or two kinds.
4, preparation method as claimed in claim 1 is characterized in that: residual catalyst reacts in the product that the ring-opening polymerization in the described step (2) obtains by step (1).
5, preparation method as claimed in claim 1 is characterized in that: expoxy propane, oxirane add at interval in the described step (2), form the poly-alkoxyl ether of polyglycerol of block polymerization.
6, preparation method as claimed in claim 1 is characterized in that: described C
12～C
22Aliphatic acid is one or more in straight chain, side chain, saturated, the unrighted acid arbitrarily.
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| CN2008101214676A CN101376089B (en) | 2008-09-28 | 2008-09-28 | Method for preparing foam killer |
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|---|---|---|---|
| CN2008101214676A CN101376089B (en) | 2008-09-28 | 2008-09-28 | Method for preparing foam killer |
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| CN101376089B CN101376089B (en) | 2010-09-29 |
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| CN101664655B (en) * | 2009-09-10 | 2011-11-16 | 沧州信昌化工有限公司 | Composite silicon-free defoamer |
| CN102286146A (en) * | 2011-05-04 | 2011-12-21 | 湖北富邦科技股份有限公司 | Preparation method of defoaming agent for producing phosphoric acid by wet process |
| CN102580361A (en) * | 2012-02-21 | 2012-07-18 | 广州甘蔗糖业研究所 | Defoaming agent for sugar industry and preparation method for defoaming agent |
| CN103476267A (en) * | 2011-03-23 | 2013-12-25 | 理研维他命股份有限公司 | Defoaming agent for food |
| CN105036227A (en) * | 2015-07-21 | 2015-11-11 | 安徽江威精密制造有限公司 | Waste water anti-foaming agent and preparing method thereof |
| CN105315453A (en) * | 2015-11-25 | 2016-02-10 | 山东一诺威新材料有限公司 | Polyglycerol polyether polyol and preparation method thereof |
| CN106669239A (en) * | 2016-12-28 | 2017-05-17 | 广东中联邦精细化工有限公司 | Defoaming agent for building materials and preparation method of defoaming agent |
| CN106807117A (en) * | 2016-12-27 | 2017-06-09 | 广东中联邦精细化工有限公司 | A kind of wiring board cleans special defoamer |
| CN107034727A (en) * | 2017-04-26 | 2017-08-11 | 威尔（福建）生物有限公司 | A kind of defoamer and its synthetic method |
| JPWO2016136437A1 (en) * | 2015-02-28 | 2017-12-07 | サンノプコ株式会社 | Antifoaming improver, antifoaming agent containing the same, and aqueous coating composition |
| CN110252098A (en) * | 2018-03-12 | 2019-09-20 | 山东奥古生物科技有限公司 | A kind of air cleaning cream and preparation method thereof |
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| CN111534360A (en) * | 2020-03-05 | 2020-08-14 | 郑州大学 | Water-based antirust defoaming agent and preparation method thereof |
| CN113908593A (en) * | 2021-10-14 | 2022-01-11 | 北京环水清科技有限公司 | Defoaming agent for treating high-concentration organic wastewater and preparation method thereof |
| CN116445223A (en) * | 2023-04-19 | 2023-07-18 | 脂代生物科技(杭州)有限公司 | Preparation method of propoxyl glycerin fatty acid ester |
| WO2024057984A1 (en) * | 2022-09-13 | 2024-03-21 | Ａｇｃ株式会社 | Method for producing polyether polyol, method for producing polyether polyol having reactive silicon group, and polyether polyol |
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| EP4135868A1 (en) * | 2020-04-14 | 2023-02-22 | Dow Global Technologies LLC | Foam control agent based on polyglycerol ether and use in bioethanol processing |
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2008
- 2008-09-28 CN CN2008101214676A patent/CN101376089B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101664655B (en) * | 2009-09-10 | 2011-11-16 | 沧州信昌化工有限公司 | Composite silicon-free defoamer |
| CN103476267A (en) * | 2011-03-23 | 2013-12-25 | 理研维他命股份有限公司 | Defoaming agent for food |
| CN103476267B (en) * | 2011-03-23 | 2014-10-22 | 理研维他命股份有限公司 | Defoaming agent for food |
| CN102286146A (en) * | 2011-05-04 | 2011-12-21 | 湖北富邦科技股份有限公司 | Preparation method of defoaming agent for producing phosphoric acid by wet process |
| CN102580361A (en) * | 2012-02-21 | 2012-07-18 | 广州甘蔗糖业研究所 | Defoaming agent for sugar industry and preparation method for defoaming agent |
| CN102580361B (en) * | 2012-02-21 | 2014-07-30 | 广州甘蔗糖业研究所 | Defoaming agent for sugar industry and preparation method for defoaming agent |
| JPWO2016136437A1 (en) * | 2015-02-28 | 2017-12-07 | サンノプコ株式会社 | Antifoaming improver, antifoaming agent containing the same, and aqueous coating composition |
| CN105036227A (en) * | 2015-07-21 | 2015-11-11 | 安徽江威精密制造有限公司 | Waste water anti-foaming agent and preparing method thereof |
| CN105315453A (en) * | 2015-11-25 | 2016-02-10 | 山东一诺威新材料有限公司 | Polyglycerol polyether polyol and preparation method thereof |
| CN105315453B (en) * | 2015-11-25 | 2017-07-14 | 山东一诺威新材料有限公司 | Polyglycerol based polyether polyol and preparation method thereof |
| CN106807117A (en) * | 2016-12-27 | 2017-06-09 | 广东中联邦精细化工有限公司 | A kind of wiring board cleans special defoamer |
| CN106669239A (en) * | 2016-12-28 | 2017-05-17 | 广东中联邦精细化工有限公司 | Defoaming agent for building materials and preparation method of defoaming agent |
| CN107034727A (en) * | 2017-04-26 | 2017-08-11 | 威尔（福建）生物有限公司 | A kind of defoamer and its synthetic method |
| CN110252098A (en) * | 2018-03-12 | 2019-09-20 | 山东奥古生物科技有限公司 | A kind of air cleaning cream and preparation method thereof |
| CN110250844A (en) * | 2019-04-15 | 2019-09-20 | 厦门磊莎茶具有限公司 | A kind of beer cup |
| CN111534360A (en) * | 2020-03-05 | 2020-08-14 | 郑州大学 | Water-based antirust defoaming agent and preparation method thereof |
| CN113908593A (en) * | 2021-10-14 | 2022-01-11 | 北京环水清科技有限公司 | Defoaming agent for treating high-concentration organic wastewater and preparation method thereof |
| WO2024057984A1 (en) * | 2022-09-13 | 2024-03-21 | Ａｇｃ株式会社 | Method for producing polyether polyol, method for producing polyether polyol having reactive silicon group, and polyether polyol |
| CN116445223A (en) * | 2023-04-19 | 2023-07-18 | 脂代生物科技(杭州)有限公司 | Preparation method of propoxyl glycerin fatty acid ester |
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