CN104437237A - Amphoteric heterogemini surfactant based on quaternary ammonium salt-phosphate and preparation method thereof - Google Patents
Amphoteric heterogemini surfactant based on quaternary ammonium salt-phosphate and preparation method thereof Download PDFInfo
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- CN104437237A CN104437237A CN201410664992.8A CN201410664992A CN104437237A CN 104437237 A CN104437237 A CN 104437237A CN 201410664992 A CN201410664992 A CN 201410664992A CN 104437237 A CN104437237 A CN 104437237A
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Abstract
The invention relates to a method for preparing an amphoteric heterogemini surfactant based on quaternary ammonium salt-phosphate. The designed heterogemini surfactant with a novel structure has important practical significance for researching the interaction force between molecules in micelles and orderly formation of an aggregate. The method comprises the following steps: preparing a mixed solvent for dissolving stearic acid monoethanolamine or erucic acid monoethanolamine; adding a phosphaticing reagent phosphorus oxychloride under nitrogen protection, reacting at the temperature of 0 DEG C, adding ethylene glycol serving as a coupling group and a quaternization reagent hexadecyl dimethyl tertiary amine, heating and reacting; performing repeated recrystallization, purifying to obtain the amphoteric heterogemini surfactant. A short coupling link of the ethylene glycol is introduced into the surfactant molecule, and ionic head groups such as the quaternary ammonium group and the phosphate group are directly connected. Compared with a single link surfactant or a symmetrical gemini surfactant of the same mole or mass concentration, the amphoteric heterogemini surfactant can effectively reduce the surface tension, can be adsorbed to the interface and has excellent surface properties.
Description
Technical field
the present invention relates to a kind of surfactant, be specifically related to a kind of based on quaternary ammonium salt-phosphatic both sexes heterogemini surfactant and preparation method thereof.
Background technology
Gemini surface active agent is the novel surfactant that a class has special construction, relative to conventional surfactant, at least containing two hydrophilic radicals and two hydrophobic groupings in its molecule.This special chemical constitution, make it have the performance more excellent than conventional surfactant, as low in critical micelle concentration, form that micella ability is strong, surface-active is high, emulsibility is good, solubilising and favorable dispersibility etc., the coupling link existed in molecular structure is understood affect its self-organizing behavior strongly.Wherein, molecular structure dissymmetric gemini surfactant, i.e. heterogemini surfactant, there is the head base of different chemical structures, the alkane main chain of different length and the various coupling link of change, this means that their controllable factors on molecular structure are also enriched than the Gemini surface active agent of symmetric form.Therefore, design has the heterogemini surfactant of novel structure, the configuration of their stacked arrangement in micelle and in surface absorbed layer not only can be improved from structure control, also can promote its gathering in body phase and superficial layer, the orderly formation for the interaction force between research micella Middle molecule and aggregation has important practical significance.
Summary of the invention
The object of this invention is to provide a kind of based on quaternary ammonium salt-phosphatic both sexes heterogemini surfactant and preparation method thereof, can more effectively reduce surface tension and be adsorbed on interface, there is more excellent surface property.
The technical solution adopted in the present invention is:
Based on the preparation method of quaternary ammonium salt-phosphatic both sexes heterogemini surfactant, it is characterized in that:
Realized by following steps:
Step one: configuration mixed solvent, dissolves stearic acid MEA or the erucic acid MEA of 100 parts, is transferred to until completely dissolved in flask;
Step 2: under nitrogen protection, add the phosphorylation agent POCl3 of 120 ~ 130 parts, after reacting 3 ~ 5h at 0 DEG C, add 95 ~ 105 parts of ethylene glycol as connection base, the quaternizing agent hexadecyldimethyl benzyl ammonium tertiary amine of 95 ~ 105 parts, is warmed up to 60 ~ 70 DEG C of reaction 36h;
Step 3: step 2 products therefrom adopts acetone, acetonitrile is recrystallized repeatedly, obtains purified product, dry in vacuum drying chamber, the volatile solvent in removing mixture, obtains both sexes heterogemini surfactant.
In step one, mixed solvent is the mixture of oxolane, ether and acetonitrile, and mixed volume is than being 1:1:1.
The described both sexes heterogemini surfactant obtained based on the preparation method of quaternary ammonium salt-phosphatic both sexes heterogemini surfactant.
The present invention has the following advantages:
The present invention introduces the short coupling link of ethylene glycol in surfactant molecule, and be directly connected to quaternary ammonium group and phosphate-based two ion head bases, the both sexes heterogemini surfactant of preparation is compared with symmetric form Gemini surface active agent with the single linked list surface-active agent of identical mole or mass concentration, more effectively can reduce surface tension and be adsorbed on interface, there is more excellent surface property.
The present invention uses natural acid MEA for raw material, phosphorylation reaction is passed through in the macromolecular chain of its aliphatic acid, first introduce hydrophilic phosphate group, then introducing ethylene glycol is short coupling link, hexadecyldimethyl benzyl ammonium tertiary amine is added again by quaternized, obtain a kind of based on quaternary ammonium salt-phosphatic both sexes heterogemini surfactant, the both sexes heterogemini surfactant of preparation not only has the performance more excellent than the Gemini surface active agent of symmetric form, can also by regulating and controlling the alkyl chain structure of aliphatic acid and tertiary amine, improve the configuration of their stacked arrangement in micelle and in surface absorbed layer, for the orderly formation of the interaction force between research micella Middle molecule and aggregation lays the foundation.
Detailed description of the invention
Below in conjunction with detailed description of the invention, the present invention will be described in detail.
The preparation method based on quaternary ammonium salt-phosphatic both sexes heterogemini surfactant that the present invention relates to, by phosphorylation and quaternized, with ethylene glycol be connect base connect hydrophilic phosphate and quaternary ammonium group, prepare a kind of structure-controllable, function admirable based on quaternary ammonium salt-phosphate both sexes heterogemini surfactant.Specifically obtained by following steps:
Step one: configuration mixed solvent, dissolves stearic acid MEA or the erucic acid MEA of 100 parts, is transferred to until completely dissolved (mixed solvent consumption is the consumption that can dissolve stearic acid MEA or erucic acid MEA completely) in flask;
Step 2: under nitrogen protection, add the phosphorylation agent POCl3 of 120 ~ 130 parts, after reacting 3 ~ 5h at 0 DEG C, add 95 ~ 105 parts of ethylene glycol as connection base, the quaternizing agent hexadecyldimethyl benzyl ammonium tertiary amine of 95 ~ 105 parts, is warmed up to 60 ~ 70 DEG C of reaction 36h;
Step 3: step 2 products therefrom adopts acetone, acetonitrile is recrystallized repeatedly, obtains purified product, dry in vacuum drying chamber, the volatile solvent in removing mixture, obtains both sexes heterogemini surfactant.
In step one, mixed solvent is the mixture of oxolane, ether and acetonitrile, and mixed volume is than being 1:1:1.
Embodiment 1:
Step one: configuration mixed solvent, dissolves the stearic acid MEA of 100 parts, is transferred to until completely dissolved in flask;
Step 2: under nitrogen protection, adds the phosphorylation agent POCl3 of 120 parts, after reacting 5h, adds 95 parts of ethylene glycol as connection base, the quaternizing agent hexadecyldimethyl benzyl ammonium tertiary amine of 105 parts, be warmed up to 60 DEG C of reaction 36h at 0 DEG C;
Step 3: step 2 products therefrom adopts acetone, acetonitrile is recrystallized repeatedly, obtains purified product, dry in vacuum drying chamber, the volatile solvent in removing mixture, obtains both sexes heterogemini surfactant.
In step one, mixed solvent is the mixture of oxolane, ether and acetonitrile, and mixed volume is than being 1:1:1.
Embodiment 2:
Step one: configuration mixed solvent, dissolves the erucic acid MEA of 100 parts, is transferred to until completely dissolved in flask;
Step 2: under nitrogen protection, adds the phosphorylation agent POCl3 of 125 parts, after reacting 4h, adds 100 parts of ethylene glycol as connection base, the quaternizing agent hexadecyldimethyl benzyl ammonium tertiary amine of 100 parts, be warmed up to 65 DEG C of reaction 36h at 0 DEG C;
Step 3: step 2 products therefrom adopts acetone, acetonitrile is recrystallized repeatedly, obtains purified product, dry in vacuum drying chamber, the volatile solvent in removing mixture, obtains both sexes heterogemini surfactant.
In step one, mixed solvent is the mixture of oxolane, ether and acetonitrile, and mixed volume is than being 1:1:1.
Embodiment 3:
Step one: configuration mixed solvent, dissolves the erucic acid MEA of 100 parts, is transferred to until completely dissolved in flask;
Step 2: under nitrogen protection, adds the phosphorylation agent POCl3 of 130 parts, after reacting 3h, adds 105 parts of ethylene glycol as connection base, the quaternizing agent hexadecyldimethyl benzyl ammonium tertiary amine of 95 parts, be warmed up to 70 DEG C of reaction 36h at 0 DEG C;
Step 3: step 2 products therefrom adopts acetone, acetonitrile is recrystallized repeatedly, obtains purified product, dry in vacuum drying chamber, the volatile solvent in removing mixture, obtains both sexes heterogemini surfactant.
In step one, mixed solvent is the mixture of oxolane, ether and acetonitrile, and mixed volume is than being 1:1:1.
According to preparation method of the present invention prepare based on quaternary ammonium salt-phosphatic heterogemini surfactant, the Gemini surface active agent of its Performance Ratio symmetric form is excellent, can also pass through to regulate the alkyl chain of aliphatic acid and tertiary amine to control the structure of heterogemini surfactant, significant for the interaction force between research its micella pattern formed and micella.
Detect the performance based on quaternary ammonium salt-phosphatic both sexes heterogemini surfactant adopting the inventive method to prepare according to GB QB/T1323-1991, GB/T7462-1994 and GB5557-1985 etc., its critical micelle concentration is minimum reaches 5 × 10
-4molL
-1, there is higher surface-active; Its foaming power is between 1.3 ~ 2.0 times, and steady bubble power is between 0.5 ~ 1.0 times, and its foaming properties belongs to medium; Its emulsifiability is tested, and can reach more than 200s, and the wetting testing time, within 8s, has good emulsifiability and wettability.
Content of the present invention is not limited to cited by embodiment, and the conversion of those of ordinary skill in the art by reading description of the present invention to any equivalence that technical solution of the present invention is taked, is claim of the present invention and contains.
Claims (3)
1., based on the preparation method of quaternary ammonium salt-phosphatic both sexes heterogemini surfactant, it is characterized in that:
Realized by following steps:
Step one: configuration mixed solvent, dissolves stearic acid MEA or the erucic acid MEA of 100 parts, is transferred to until completely dissolved in flask;
Step 2: under nitrogen protection, add the phosphorylation agent POCl3 of 120 ~ 130 parts, after reacting 3 ~ 5h at 0 DEG C, add 95 ~ 105 parts of ethylene glycol as connection base, the quaternizing agent hexadecyldimethyl benzyl ammonium tertiary amine of 95 ~ 105 parts, is warmed up to 60 ~ 70 DEG C of reaction 36h;
Step 3: step 2 products therefrom adopts acetone, acetonitrile is recrystallized repeatedly, obtains purified product, dry in vacuum drying chamber, the volatile solvent in removing mixture, obtains both sexes heterogemini surfactant.
2. the preparation method based on quaternary ammonium salt-phosphatic both sexes heterogemini surfactant according to claim 1, is characterized in that:
In step one, mixed solvent is the mixture of oxolane, ether and acetonitrile, and mixed volume is than being 1:1:1.
3. the both sexes heterogemini surfactant obtained based on the preparation method of quaternary ammonium salt-phosphatic both sexes heterogemini surfactant according to claim 2.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106283638A (en) * | 2016-08-11 | 2017-01-04 | 福建昆冈化学助剂科技有限公司 | A kind of weaving penetrating agent and preparation method thereof |
| CN108047269A (en) * | 2018-01-05 | 2018-05-18 | 山东大学 | A kind of quaternary Hydroxypropyl phosphate ester sodium splits type asphalt emulsifier and preparation method thereof soon |
| CN109111908A (en) * | 2018-07-26 | 2019-01-01 | 东营利丰化工新材料有限公司 | A kind of oil field increasing injection double type surfactant system and preparation method thereof |
| CN111408314A (en) * | 2020-04-17 | 2020-07-14 | 甘肃智仑新材料科技有限公司 | Alkynyl-containing cationic surfactant and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103521125A (en) * | 2013-10-25 | 2014-01-22 | 陕西科技大学 | Method for preparing oleic acid Gemini surfactant |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103521125A (en) * | 2013-10-25 | 2014-01-22 | 陕西科技大学 | Method for preparing oleic acid Gemini surfactant |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106283638A (en) * | 2016-08-11 | 2017-01-04 | 福建昆冈化学助剂科技有限公司 | A kind of weaving penetrating agent and preparation method thereof |
| CN106283638B (en) * | 2016-08-11 | 2018-07-24 | 福建昆冈化学助剂科技有限公司 | A kind of weaving bleeding agent and preparation method thereof |
| CN108047269A (en) * | 2018-01-05 | 2018-05-18 | 山东大学 | A kind of quaternary Hydroxypropyl phosphate ester sodium splits type asphalt emulsifier and preparation method thereof soon |
| CN108047269B (en) * | 2018-01-05 | 2019-08-13 | 山东大学 | A kind of quaternary Hydroxypropyl phosphate ester sodium splits type asphalt emulsifier and preparation method thereof fastly |
| CN109111908A (en) * | 2018-07-26 | 2019-01-01 | 东营利丰化工新材料有限公司 | A kind of oil field increasing injection double type surfactant system and preparation method thereof |
| CN111408314A (en) * | 2020-04-17 | 2020-07-14 | 甘肃智仑新材料科技有限公司 | Alkynyl-containing cationic surfactant and preparation method thereof |
| CN111408314B (en) * | 2020-04-17 | 2021-08-10 | 甘肃智仑新材料科技有限公司 | Alkynyl-containing cationic surfactant and preparation method thereof |
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Application publication date: 20150325 |