CN106854276A - One kind C36The method that dimer (fatty acid) yl prepares amphoteric polymeric surfactant - Google Patents
One kind C36The method that dimer (fatty acid) yl prepares amphoteric polymeric surfactant Download PDFInfo
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- CN106854276A CN106854276A CN201510894198.7A CN201510894198A CN106854276A CN 106854276 A CN106854276 A CN 106854276A CN 201510894198 A CN201510894198 A CN 201510894198A CN 106854276 A CN106854276 A CN 106854276A
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Abstract
The invention discloses one kind with C36Dimer (fatty acid) yl is the method for preparing surfactant, is comprised the following steps：1）C is prepared using direct polycondensation method36The polyester of dimer (fatty acid) yl and polyethylene glycol；2) step 1）Product prepares amphoteric polymeric surfactant-C with sulfamic acid reaction36Dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid.
Description
Technical field
The invention provides one kind with C36The method that dimer (fatty acid) yl prepares amphoteric polymeric surfactant for raw material, is related to the technical fields such as oil chemistry, high molecular surfactant.
Background technology
Dimer (fatty acid) yl is natural oil chemical products, and its toxicity is low, wide material sources and raw material is renewable, is the raw material of excellent synthesizing new macromolecular material.Dimer (fatty acid) yl also has good water resistance and sealing, has strong adhesiveness to materials such as metals, and toxicity is low, nonflammable, and -20 DEG C do not crystallize, do not lose transparent flow, 250 DEG C do not evaporate, the good characteristic such as not gelation.By dimer (fatty acid) yl and the polyester of polyethylene glycol reaction generation; both the lipophilic group in certain rigidity and steric hindrance is contained in molecule; also contain hydrophilic polyether chain; so being a kind of ester ether non-ionic (polymeric surfactant); it has the performance of aliphatic alcohols and polyether surfactant compounding use; because its molecular weight is big; with unexistent some characteristics of low-molecular-weight surfactant; such as good foam stabilizing power, wetability, emulsification and thickening power; small toxicity; there is good protecting colloid and solubilising power, be used widely in numerous industrial circles.
C36Dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid is with C36Dimer (fatty acid) yl and polyethylene glycol are raw material, by factors such as the mol ratios both controlling during polycondensation, are prepared for that relative molecular mass is larger and polyester in narrow ditribution, then again with the terminal hydroxy group of the selectively sulfated polyester of sulfamic acid improving its hydrophilicity.The difference of the technique of polycondensation and synthesis condition in synthesizing polyester sulfuric acid, influences the property and application performance of polyester sulfuric acid.
Polyester sulfuric acid is a kind of new amphoteric polymeric surfactant, and it had both had the property of nonionic surfactant, it may have some characteristics of anion surfactant, showed excellent application performance.Its toxicity is low, biological degradability and environment affinity are good.At present, it is main Material synthesis surfactant with dimeric dibasic acid, particularly synthesizes the research work of high molecular surfactant, it is domestic there is not yet document report, still belongs to the first time in China, with great social effect and wide application prospect.
Description
It is an object of the invention to provide one kind with C36The method that dimer (fatty acid) yl prepares amphoteric polymeric surfactant for raw material, with C36Dimer (fatty acid) yl, polyethylene glycol, sulfamic acid are raw material, under catalyst action, the reaction rule of synthesizing polyester is analyzed by studying different catalysts concentration, reaction time, reaction temperature, reactant ratio to the esterification yield influence of polymerisation, is that the preparation condition of synthesizing polyester is referred to.By the selectivity of sulfamic acid, C is improved36The hydrophilicity of dimer fatty acid polyethylene glycol, synthesizes a kind of low toxicity, biological degradability and a kind of good new type amphoteric high molecular surfactant of environment affinity.
The purpose of the present invention is achieved through the following technical solutions.
One kind is with C36The method that dimer (fatty acid) yl prepares amphoteric polymeric surfactant for raw material, it is characterised in that comprise the following steps：
1）C is prepared using direct polycondensation method36The polyester of dimer (fatty acid) yl and polyethylene glycol；
2）Step 1）Product prepares amphoteric polymeric surfactant with sulfamic acid reaction --- C36Dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid.
The step 1）Utilization direct polycondensation method prepare C36The polyester of dimer (fatty acid) yl and polyethylene glycol refers to the C that certain mol proportion is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst, vacuumize, and stirring reaction certain hour, obtains C under certain reaction temperature36Dimeric dibasic acid polyethylene glycol polyester；
The step 2）Step 1）Product prepares amphoteric polymeric surfactant with sulfamic acid reaction --- C36Dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid refers to add C in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, then the sulfamic acid by grinding is quantitatively adding, catalyst is put into the oil bath of constant temperature, is reacted under the conditions of certain reaction time and polymerization temperature, question response generation C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, calculate the esterification yield of product, and surface-active analysis is carried out to product.
The step 1）The molar ratio of middle dimer (fatty acid) yl and polyethylene glycol is 1: 0.05 ~ 5.5.
The step 1）Middle catalyst is stannous chloride, and consumption is the 0.05% ~ 4.5% of reactant gross mass.
The step 1）Middle reaction temperature is 150 ~ 230 DEG C.
The step 1）The middle reaction time is 4.5 ~ 8h.
The step 2）Middle catalyst is urea.
The step 2）Middle C36The molar ratio of dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and catalyst is 1: 0.05 ~ 5.5: 0.05 ~ 4.5.
The step 2）Middle reaction temperature is 80 ~ 180 DEG C.
The step 2）The middle reaction time is 0.5 ~ 6.5h.
Prior art of the present invention is compared to advantages below：
The present invention uses C36Dimer (fatty acid) yl, polyethylene glycol are raw material, under catalyst action, prepare polyester by polycondensation reaction, then prepare polyester sulfuric acid, i.e. amphoteric polymeric surfactant with sulfamic acid acidifying.Mainly by first preparing C36The polyester of dimer (fatty acid) yl and polyethylene glycol, then prepare polyester sulfuric acid with sulfamic acid acidifying, that is, prepare amphoteric polymeric surfactant.Especially with the C that addition molar ratio in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask is 1: 1.236Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, and 4.5 ~ 8h of stirring reaction under the conditions of being 150 ~ 230 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1: 0.05 ~ 5.5: 0.05 ~ 4.5 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, 0.5 ~ 6.5h of stirring reaction under conditions of 80 ~ 180 DEG C, question response generation C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, calculate the esterification yield of product, and surface-active analysis is carried out to product.
As can be seen here, the primary raw material that the present invention is used is C36Dimer (fatty acid) yl, polyethylene glycol and sulfamic acid, first by C36Dimer (fatty acid) yl is polymerized with polyethylene glycol, obtains C36Dimer (fatty acid) yl polyethylene glycol polyester, is then acidified C with sulfamic acid36Dimer (fatty acid) yl polyethylene glycol polyester, has obtained low toxicity, the amphoteric polymeric surfactant with good biodegradability properties, foam stabilizing power, wetability, environment affinity, emulsification and thickening power.The moisture of reaction generation can be excluded directly to vacuumize instead of nitrogen protection all the time in course of reaction, the oxidation of reactant is avoided that again, simplify synthesis technique, reduce reaction cost, environmental protection and energy saving.With urea as catalyst, reaction is carried out to the direction of generation polyester sulfate, be conducive to the raising of esterification yield, and greatly improve the appearance luster of product.With sulfamic acid as sulfur acidizing reagent, terminal hydroxy group can be well acidified, phenyl ring or double bond are not influenceed, product purity is high, easy to operate, and can easily control Sulfation depth according to different requirements；If desired other salts, can easily convert.
Specific embodiment
The present invention is illustrated below by way of specific embodiment, but the present invention is not merely defined in these embodiments.
Embodiment
1
The C that molar ratio is 1: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, is vacuumized, and stirring reaction 6h under the conditions of being 200 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1: 1: 1.1 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, the stirring reaction 3h under conditions of 150 DEG C.Question response generates C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, the esterification yield for being computed product is 50.29%.
Embodiment
2
The C that molar ratio is 1: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, is vacuumized, and stirring reaction 6h under the conditions of being 200 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1: 1: 0.9 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, the stirring reaction 3h under conditions of 130 DEG C.Question response generates C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, the esterification yield for being computed product is 55.02%.
Embodiment
3
The C that molar ratio is 1: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, is vacuumized, and stirring reaction 6h under the conditions of being 200 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1: 1.15: 1.1 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, the stirring reaction 1h under conditions of 130 DEG C.Question response generates C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, the esterification yield for being computed product is 61.84%.
Embodiment
4
The C that molar ratio is 1: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, is vacuumized, and stirring reaction 6h under the conditions of being 200 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1: 1: 1.1 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, the stirring reaction 3h under conditions of 120 DEG C.Question response generates C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, the esterification yield for being computed product is 69.90%.
Embodiment
5
The C that molar ratio is 1: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, is vacuumized, and stirring reaction 6h under the conditions of being 200 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1: 1: 1.1 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, the stirring reaction 3h under conditions of 130 DEG C.Question response generates C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, the esterification yield for being computed product is 74.03%.
Embodiment
6
The C that molar ratio is 1: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, is vacuumized, and stirring reaction 6h under the conditions of being 200 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1: 1.15: 1.1 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, the stirring reaction 2h under conditions of 130 DEG C.Question response generates C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, the esterification yield for being computed product is 78.56%.
Embodiment
7
The C that molar ratio is 1: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimer (fatty acid) yl and polyethylene glycol, add catalyst stannous chloride, and addition is the 0.3% of reactant gross mass, is vacuumized, and stirring reaction 6h under the conditions of being 200 DEG C in reaction temperature obtains C36Dimeric dibasic acid polyethylene glycol polyester；Then the C that molar ratio is 1.0: 1.2: 1.2 is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask36Dimeric dibasic acid polyethylene glycol polyester, sulfamic acid and urea, are put into the oil bath of constant temperature, the stirring reaction 2.8h under conditions of 130 DEG C, question response generation C36Stop reaction after dimer (fatty acid) yl polyethylene glycol polyester sulfuric acid, the esterification yield for being computed product is 81.17%.At 25 DEG C, surface tension during critical micelle concentration is 3.021mN/m to product, with K12Quite；CMC is 1.07mmol/L, far below K12；Emulsifiability and emulsion stability are suitable with OP-10；With K12Compare, product shows good suds suppressing properties.
Claims (9)
1. a kind of method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls, it is characterised in that comprise the following steps：
1）The polyester of C36 dimer (fatty acid) yls and polyethylene glycol is prepared using direct polycondensation method；
2）Step 1）Product prepares amphoteric polymeric surfactant with sulfamic acid reaction --- C36 dimer (fatty acid) yl polyethylene glycol polyester sulfuric acids；
The step 1）The polyester for preparing C36 dimer (fatty acid) yls and polyethylene glycol using direct polycondensation method refer to the C36 dimer (fatty acid) yls and polyethylene glycol that certain mol proportion is added in the reaction vessel equipped with condensing unit, vacuum plant, thermometer, agitating device, oil bath heating device and flask, add catalyst, vacuumize, the stirring reaction certain hour under certain reaction temperature, obtains C36 dimeric dibasic acid polyethylene glycol polyesters；
The step 2）Step 1）Product prepares amphoteric polymeric surfactant with sulfamic acid reaction --- and C36 dimer (fatty acid) yl polyethylene glycol polyester sulfuric acids refer to equipped with condensing unit, vacuum plant, thermometer, agitating device, C36 dimeric dibasic acid polyethylene glycol polyesters are added in the reaction vessel of oil bath heating device and flask, the sulfamic acid by grinding is quantitatively adding again, catalyst, it is put into the oil bath of constant temperature, reacted under the conditions of certain reaction time and polymerization temperature, stop reaction after question response generation C36 dimer (fatty acid) yl polyethylene glycol polyester sulfuric acids, calculate product esterification yield, and surface-active analysis is carried out to product.
2. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 1）The mol ratio of middle dimer (fatty acid) yl and polyethylene glycol is 1: 0.05 ~ 5.5.
3. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 1）Middle catalyst is stannous chloride, and consumption is the 0.05% ~ 4.5% of reactant gross mass.
4. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 1）Middle reaction temperature is 150 ~ 230 DEG C.
5. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 1）The middle reaction time is 4.5 ~ 8h.
6. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 2）Middle catalyst is urea.
7. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 2）The molar ratio of middle C36 dimeric dibasic acids polyethylene glycol polyester, sulfamic acid and catalyst is 1: 0.05 ~ 5.5: 0.05 ~ 4.5.
8. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 2）Middle reaction temperature is 80 ~ 180 DEG C.
9. the method for preparing amphoteric polymeric surfactant as raw material with C36 dimer (fatty acid) yls according to claim 1, it is characterised in that：The step 2）The middle reaction time is 0.5 ~ 6.5h.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510894198.7A CN106854276A (en) | 2015-12-08 | 2015-12-08 | One kind C36The method that dimer (fatty acid) yl prepares amphoteric polymeric surfactant |
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| CN201510894198.7A CN106854276A (en) | 2015-12-08 | 2015-12-08 | One kind C36The method that dimer (fatty acid) yl prepares amphoteric polymeric surfactant |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019222956A1 (en) * | 2018-05-24 | 2019-11-28 | Evonik Specialty Chemicals (Shanghai) Co., Ltd. | Polyester thickeners with self-levelling elastic gelling ability |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4195000A (en) * | 1978-03-17 | 1980-03-25 | Gaf Corporation | Impact modified thermoplastic copolyester |
| CN101205292A (en) * | 2007-12-07 | 2008-06-25 | 南京工业大学 | Dimer acid polyester polyhydric alcohols and preparation thereof |
| CN104277816A (en) * | 2014-10-08 | 2015-01-14 | 西南石油大学 | Sulfonate type amphoteric high-molecular surfactant and synthesis method thereof |
-
2015
- 2015-12-08 CN CN201510894198.7A patent/CN106854276A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4195000A (en) * | 1978-03-17 | 1980-03-25 | Gaf Corporation | Impact modified thermoplastic copolyester |
| CN101205292A (en) * | 2007-12-07 | 2008-06-25 | 南京工业大学 | Dimer acid polyester polyhydric alcohols and preparation thereof |
| CN104277816A (en) * | 2014-10-08 | 2015-01-14 | 西南石油大学 | Sulfonate type amphoteric high-molecular surfactant and synthesis method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 冯光炷，等: "C36二聚脂肪酸聚乙二醇聚酯硫酸酯盐的制备及性能表征", 《精细化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019222956A1 (en) * | 2018-05-24 | 2019-11-28 | Evonik Specialty Chemicals (Shanghai) Co., Ltd. | Polyester thickeners with self-levelling elastic gelling ability |
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Application publication date: 20170616 |