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 PDF

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Publication number
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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allyl
fatty alcohol
ether
preparation
anion
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季永新
王也
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Nanjing Forestry University
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Nanjing Forestry University
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00Esters of sulfuric acids
    • C07C305/02Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/10Esters 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/02Preparation of ethers from oxiranes
    • C07C41/03Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/12Polymerisation in non-solvents
    • C08F2/16Aqueous medium
    • C08F2/22Emulsion polymerisation
    • C08F2/24Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/26Emulsion polymerisation with the aid of emulsifying agents anionic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/12Polymerisation in non-solvents
    • C08F2/16Aqueous medium
    • C08F2/22Emulsion polymerisation
    • C08F2/24Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/30Emulsion polymerisation with the aid of emulsifying agents non-ionic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular 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
    • C08G65/2603Macromolecular 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
    • C08G65/2606Macromolecular 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
    • C08G65/2609Macromolecular 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

A kind of allyl anion-nonionic emulsifier and preparation method thereof
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.
CN201811211913.2A 2018-10-18 2018-10-18 A kind of allyl anion-nonionic emulsifier and preparation method thereof Pending CN109369470A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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CN107419563A (en) * 2017-06-19 2017-12-01 苏州世名科技股份有限公司 A kind of polymer overmold dispersible pigment color paste and preparation method thereof
CN108442141A (en) * 2018-03-20 2018-08-24 东莞长联新材料科技股份有限公司 A kind of environment-friendly type printing and dyeing special-purpose high temperature foaming slurry and preparation method thereof

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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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