CN109369470A - A kind of allyl anion-nonionic emulsifier and preparation method thereof - Google Patents
A kind of allyl anion-nonionic emulsifier and preparation method thereof Download PDFInfo
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- CN109369470A CN109369470A CN201811211913.2A CN201811211913A CN109369470A CN 109369470 A CN109369470 A CN 109369470A CN 201811211913 A CN201811211913 A CN 201811211913A CN 109369470 A CN109369470 A CN 109369470A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention discloses a kind of allyl anion-nonionic emulsifier and preparation method thereof, the structural formulas of the emulsifier are as follows:
Description
Technical field
The present invention relates to a kind of allyl anion-nonionic emulsifiers and preparation method thereof, belong to fine chemistry industry chemicals
Field.
Background technique
Emulsifier is one of the main component in emulsion polymerization systems, plays decisive role to the performance of polymer.It is existing
Some emulsifiers are mostly anionic emulsifier, nonionic emulsifier, this kind of emulsifier do not have non-ionic group or yin from
Subbase group, emulsion stability, lotion electrolyte-resistant and water solubility etc. are relatively poor, generally require the two and are used in compounding.Mesh
Preceding to study more anion-nonionic type emulsifier both at home and abroad as maleic acid ester emulsifying agent, such emulsifier mainly uses C12-
C16 straight chain primary alcohol/alcohol ether, alkyl phenol polyoxyethylene ether are starting material, are obtained through maleated.It is closed in addition, remaining dragon flies to wait
At a kind of light base propyl sulfonic acid salt anion-nonionic type reactive emulsifier of maleic acid list secondary alcohol polyoxyethylene ether -2-, due to
There is water in synthesis process, so containing admittedly for emulsifier is lower, drying program is complicated, and use is not convenient enough.
The allyl yin-prepared using the allyl fatty alcohol ether after sulfamic acid, urea and addition as starting material it is non-from
Sub- emulsifier due to containing non-ionic group, anionic group, unsaturated double-bond, thus has anionic emulsifier or non-
The performances such as the incomparable more excellent cold-resistant, electrolyte-resistant of ionic emulsifying agent and mechanical resistant shearing, can be widely applied to
The fields such as detergent, ink, coating and emulsion polymerization.
Summary of the invention
For problem and shortage existing for existing emulsifier, the invention discloses a kind of allyl anion-nonionic emulsifiers
And preparation method thereof, the allyl anion-nonionic emulsifier preparation method is simple, and low energy consumption for synthesis technology, catalyst and centre
Product small toxicity, whole production process environment-friendly and green is pollution-free.
In order to solve the above technical problems, the invention adopts the following technical scheme:
A kind of allyl anion-nonionic emulsifier, should the alkene containing non-ionic group, anionic group and unsaturated double-bond
Propyl anion-nonionic emulsifier, structural formula are as follows:
The wherein integer that n is 8~16, the integer that m is 3~15.
A kind of preparation method of the allyl anion-nonionic emulsifier, comprising the following steps:
(1) fatty alcohol and sodium methoxide are mixed, 85~105 DEG C of dropwise addition allyl glycidyl ethers are added dropwise
After keep the temperature at 90~110 DEG C, be passed through nitrogen react 2.5~4.5h, obtain open-loop products i.e. allyl
Isomery alcohol ether, wherein the molar ratio of fatty alcohol and allyl glycidyl ether is 1:1.05~1:1.15, and sodium methoxide is fatty alcohol
With the 0.6%~0.8% of allyl glycidyl ether quality sum;
(2) hydroxyl on the open-loop products branch in step 1 is added into ethylene oxide, wherein open-loop products and ethylene oxide
Molar ratio is 1:3~1:15, obtains the allyl fatty alcohol ether of different EO values (3~15);
(3) by after ethyleneoxide addition allyl fatty alcohol ether and urea mix, ammonia is added portionwise at 85~95 DEG C
Base sulfonic acid, after be warming up at 100~110 DEG C 2~4h of reaction, allyl fatty alcohol ether sulfuric acid amine salt is obtained, wherein after addition
The molar ratio of allyl fatty alcohol ether and sulfamic acid is 1:1.25~1:1.45, and amount of urea is allyl fatty alcohol ether and ammonia
The 2%~4% of base sulfonic acid quality sum.Thick allyl fatty alcohol ether sulfuric acid amine salt finally is dissolved with solvent, and leaches out residue
Urea and sulfamic acid, then rotate and boil off solvent, obtain allyl anion-nonionic emulsifier of the invention.
Fatty alcohol in the step 1 include Decanol, laruyl alcohol, ten alcohol of isomery, isomerous tridecanol, isomery hexadecanol,
One of isomery tetradecyl alchohol, preferably laruyl alcohol, ten alcohol of isomery, isomerous tridecanol, isomery tetradecyl alchohol, isomery hexadecanol.
Solvent in the step 3 is one of ethyl alcohol, methanol, acetone, pentanone, butanol.
Technology of the invention compared with prior art, has the beneficial effect that
1) polymerizable double bond is had in emulsifier of the invention, activity is high, energy and acrylic ester copolymer.
2) emulsifier of the invention is long-chain polyether structure, and emulsifier obtained has certain space steric stabilization.
3) emulsifier of the invention integrates anion-nonionic, emulsifier obtained have preferable cold-resistant, electrolyte-resistant and
Mechanical resistant cutting performance, and have the function of that heavy metal ion is prevented to be poisoned.
4) emulsifier stable structure of the invention, preparation flow is simple and environmentally-friendly, can be widely applied to detergent, ink, painting
The fields such as material and emulsion polymerization.
Specific embodiment
A kind of allyl anion-nonionic emulsifier, structural formula are as follows:
The wherein integer that n is 8~16, the integer that m is 3~15.
A kind of preparation method of the allyl anion-nonionic emulsifier, comprising the following steps:
(1) fatty alcohol and sodium methoxide are mixed, 85~105 DEG C of dropwise addition allyl glycidyl ethers will be warm after being added dropwise
Degree is maintained at 90~110 DEG C, is passed through nitrogen and is reacted 2.5~4.5h, obtains open-loop products i.e. allyl isomery alcohol ether, wherein rouge
The molar ratio of the pure and mild allyl glycidyl ether of fat is 1:1.05~1:1.15, and sodium methoxide is fatty alcohol and allyl glycidol
The 0.6%~0.8% of ether quality sum.
(2) hydroxyl on the open-loop products branch in step 1 is added into ethylene oxide, wherein open-loop products and ethylene oxide
Molar ratio is 1:3~1:15, obtains the allyl fatty alcohol ether of different EO values (3~15).
(3) by after ethyleneoxide addition allyl fatty alcohol ether and urea mix, ammonia is added portionwise at 85~95 DEG C
Base sulfonic acid, after be warming up at 100~110 DEG C 2~4h of reaction, allyl fatty alcohol ether sulfuric acid amine salt is obtained, wherein after addition
The molar ratio of allyl fatty alcohol ether and sulfamic acid is 1:1.25~1:1.45, and amount of urea is allyl fatty alcohol ether and ammonia
The 2%~4% of base sulfonic acid quality sum.Thick allyl fatty alcohol ether sulfuric acid amine salt finally is dissolved with solvent, and leaches out residue
Urea and sulfamic acid, then rotate and boil off solvent, obtain allyl anion-nonionic emulsifier of the invention.
In above-mentioned preparation method, it is preferred that in step 1, the fatty alcohol is laruyl alcohol, ten alcohol of isomery, isomery 13
One kind of alcohol, isomery tetradecyl alchohol, isomery hexadecanol, it is further preferred that the fatty alcohol is laruyl alcohol, ten alcohol of isomery is different
At least one of structure tridecanol.
Preferably, in step 1, the catalyst is sodium methoxide, be fatty alcohol and allyl glycidyl ether quality it
0.6%, 0.7% and the 0.8% of sum.
Preferably, in step 1, the reaction temperature is 90 DEG C, 100 DEG C and 110 DEG C.
Preferably, in step 1, the reaction time is 2.5h, 3.5h and 4.5h.
Preferably, in step 2, the open-loop products addition obtains the addition product of 3~15 EO values, further preferably
, the open-loop products addition obtains the addition product of 4~10 EO values.
Preferably, in step 3, the catalyst is urea, and amount of urea is allyl fatty alcohol ether and sulfamic acid
2%, 3% and the 4% of quality sum.
Preferably, in step 3, mole of allyl fatty alcohol ether and sulfamic acid after the sulfamic acid and addition
Than for 1:1.25,1:1.35 and 1:1.45.
Preferably, in step 3, the reaction temperature is 95 DEG C, 105 DEG C and 115 DEG C.
Preferably, in step 3, the reaction time is 2h, 3h and 4h.
Preferably, in step 3, the solvent be one of ethyl alcohol, methanol, acetone, pentanone, butanol, further
Preferably, the solvent is ethyl alcohol.
Preferably, in step 3, the purifying technique be thick allyl fatty alcohol ether sulfuric acid amine salt is dissolved with solvent, and
Remaining urea and sulfamic acid are leached out, then rotates and boils off ethyl alcohol, obtains allyl anion-nonionic emulsifier of the invention.
Combined with specific embodiments below, the content of the present invention will be further explained.
Embodiment 1
It takes 37.28g (0.2mol) laruyl alcohol and 0.437 sodium methoxide to be mixed and heated to 95 DEG C, is added dropwise 25.18g (0.22mol)
Allyl glycidyl ether obtains open-loop products after reacting 3.5h at 100 DEG C.Ethylene oxide is added to obtain open-loop products obtained
Obtain allyl laruyl alcohol (10) ether that EO value is 10.
After allyl laruyl alcohol (10) ether 44.43g (0.06mol) and the mixing of 1.569g urea after taking ethyleneoxide addition
Be heated to 85 DEG C, 7.86g (0.081mol) sulfamic acid be added, be added in three times every 15min, after be warming up to 105 DEG C, reaction
2h.Thick allyl laruyl alcohol (10) ether sulfuric acid amine salt finally is dissolved with ethyl alcohol, and leaches out remaining urea and sulfamic acid, then
Ethyl alcohol is boiled off, allyl anion-nonionic emulsifier of the invention is obtained.
In the present embodiment, selects laruyl alcohol for raw material in the preparation of allyl laruyl alcohol (10) ether ammonium sulfate salt, that is, changed
N is 12 in formula;10 ethylene oxide are added in epoxidation addition, i.e. m is 10.
Embodiment 2
It takes the pure and mild 0.250g sodium methoxide of 23.70g (0.15mol) isomery ten to be mixed and heated to 85 DEG C, 18.03g is added dropwise
(0.158mol) allyl glycidyl ether obtains open-loop products after reacting 4.5h at 90 DEG C.Open-loop products obtained are added
Ethylene oxide obtains ten alcohol of allyl isomery (7) ether that EO value is 7.
Ten alcohol of allyl isomery (7) ether 34.81g (0.06mol) and the mixing of 0.842g urea after taking ethyleneoxide addition
After be heated to 75 DEG C, 7.28g (0.075mol) sulfamic acid is added, is added in three times every 15min, after be warming up to 95 DEG C, instead
Answer 3h.Thick ten alcohol of allyl isomery (7) ether sulfuric acid amine salt finally is dissolved with ethyl alcohol, and leaches out remaining urea and amino sulphur
Acid, then rotate and boil off ethyl alcohol, obtain allyl anion-nonionic emulsifier of the invention.
In the present embodiment, selected in the preparation of ten alcohol of allyl isomery (7) ether ammonium sulfate salt ten alcohol of isomery for
Raw material, i.e., n is 10 in chemical formula;7 ethylene oxide are added in epoxidation addition, i.e. m is 7.
Embodiment 3
It takes 30.00g (0.15mol) isomerous tridecanol and 0.398g sodium methoxide to be mixed and heated to 105 DEG C, 19.75g is added dropwise
(0.173mol) allyl glycidyl ether obtains open-loop products after reacting 2.5h at 110 DEG C.Open-loop products obtained are added
Ethylene oxide obtains allyl isomerous tridecanol (4) ether that EO value is 4.
Allyl isomerous tridecanol (4) ether 24.51g (0.05mol) and 1.262g urea after taking ethyleneoxide addition is mixed
Be heated to 95 DEG C after conjunction, 7.09g (0.073mol) sulfamic acid be added, be added in three times every 15min, after be warming up to 115 DEG C,
React 4h.Thick allyl isomerous tridecanol (4) ether sulfuric acid amine salt finally is dissolved with ethyl alcohol, and leaches out remaining urea and amino
Sulfonic acid, then rotate and boil off ethyl alcohol, obtain allyl anion-nonionic emulsifier of the invention.
Select isomerous tridecanol for original in the present embodiment in the preparation of allyl isomerous tridecanol (4) ether ammonium sulfate salt
Material, i.e., n is 13 in chemical formula;4 ethylene oxide are added in epoxidation addition, i.e. m is 4.
The above is only a preferred embodiment of the present invention, it should be pointed out that: for the ordinary skill people of the art
For member, without departing from the principle of the present invention, several improvement can also be made, these improvement also should be regarded as of the invention
Protection scope.
Claims (6)
1. the invention discloses a kind of allyl anion-nonionic emulsifiers and preparation method thereof, it is characterised in that: the allyl
Anion-nonionic emulsifier is with molar ratio computing, after 1.25~1.35:0.17~0.38:1 sulfamic acid, urea and addition
Allyl fatty alcohol ether is prepared, the structural formula of emulsifier are as follows:
It is 3~15 that wherein the range of n value, which is the range of 8~16, m value,.
2. preparing the preparation method of allyl anion-nonionic emulsifier described in claim 1, it is characterised in that: including following step
It is rapid:
(1) in the reactor, fatty alcohol is added and sodium methoxide is stirred, allyl is added at 85~105 DEG C of temperature of control
Glycidol ether is passed through nitrogen and reacts 2.5~4.5h, obtain open-loop products, i.e. alkene then in the case where being kept for 90~110 DEG C of temperature
Propyl isomery alcohol ether.
(2) hydroxyl on open-loop products allyl isomery alcohol ether branch is subjected to ethyleneoxide addition reaction, obtains EO value range
For 3~15 allyl fatty alcohol ether.
(3) EO value range is mixed for 3~15 allyl fatty alcohol ether and urea, is added in batches at 85~95 DEG C of temperature of control
Enter sulfamic acid, 2~4h is reacted in the case where being kept for 100~110 DEG C of temperature, obtains thick allyl fatty alcohol ether sulfuric acid amine salt;Then
Solvent is added and dissolves thick allyl fatty alcohol ether sulfuric acid amine salt, is precipitated and filters remaining urea and sulfamic acid, finally by
Revolving removal solvent, obtains the allyl anion-nonionic emulsifier that final products are light yellow viscous liquid.
3. preparation method according to claim 2, it is characterised in that: fatty alcohol described in step (1) and allyl contracting
The molar ratio of water glycerin ether is 1:1.05~1:1.15, and sodium methoxide is fatty alcohol and allyl glycidyl ether quality sum
0.6%~0.8%.
4. preparation method according to claim 2, it is characterised in that: open-loop products allyl described in step (2) is different
The molar ratio of structure alcohol ether and ethylene oxide is 1:3~1:15.
5. preparation method according to claim 2, it is characterised in that: fatty alcohol described in step (1) include Decanol,
One of laruyl alcohol, ten alcohol of isomery, isomerous tridecanol, isomery tetradecyl alchohol, isomery hexadecanol.
6. preparation method according to claim 2, it is characterised in that: solvent described in step (3) be ethyl alcohol, methanol,
One of acetone, pentanone, butanol.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111203150A (en) * | 2020-01-03 | 2020-05-29 | 杭州詹姆森新材料科技有限公司 | Novel nonionic surfactant and preparation method thereof |
CN113307965A (en) * | 2021-05-25 | 2021-08-27 | 辽宁科隆精细化工股份有限公司 | Double-bond-containing sulfonate compound and synthesis method thereof |
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