CN106008848A - Comb type macromolecular dispersant and preparation method thereof - Google Patents

Comb type macromolecular dispersant and preparation method thereof Download PDF

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Publication number
CN106008848A
CN106008848A CN201610347276.6A CN201610347276A CN106008848A CN 106008848 A CN106008848 A CN 106008848A CN 201610347276 A CN201610347276 A CN 201610347276A CN 106008848 A CN106008848 A CN 106008848A
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preparation
macromolecule dispersing
agent
combed
dispersing agent
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Inventor
王万绪
白艳云
马晓原
杜志平
王国永
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China Daily Chemical Industry Research Institute
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China Daily Chemical Industry Research Institute
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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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

The invention relates to a comb type macromolecular dispersant, which is characterized in that the molecular structure formula is shown as the accompanying drawing, wherein m is an integer being 10 to 20; R1, R3 and R4 is H or methyl; R2 is C4-C12 alkyl groups; a, b and c are integers greater than zero. The comb type macromolecular dispersant has the advantages that the green effect is achieved; the energy is saved; the water solubility is proper; the solid content is high.

Description

A kind of combed macromolecule dispersing agent and preparation method
Technical field
The invention belongs to the additive technology field of cleaning product industry, relate generally to can be used for the comb of dispersion solid particle Type macromolecule dispersing agent and preparation method thereof.
Background technology
Surfactant is the main component of decontamination in detergent, typically with sodium alkyl sulfonate (LAS), the fatty alcohol of straight chain The non-ionic surfaces such as the anion surfactants such as polyethenoxy ether sodium sulfate (AES) and poly alkyl alcohol oxireme ether (AEO) Activating agent is composited.In washing process, anionic part surfactant, as LAS can with water substantial amounts of Ca2+、Mg2+ In conjunction with precipitating, depositing to fabric face, these deposit grain can be entered the fibrous reticular structure of medicated clothing, not only causes medicated clothing Harden, also can due to surfactant inactivation and reduce clean result.High molecular surfactant can suppress CaCO3Crystal Generation or form the less crystal grain that can suspend in water, make crystal reduce at the deposition of fiber surface, the anti-energy that hardens Power improves.
Patent CN104327203A describes with acrylic acid for polymerization monomer, with water as solvent, uses oxidization-reduction type to cause Agent, is prepared for sodium polyacrylate disperant.It is characterized in that product is excellent compared to sodium polyacrylate dispersive property on market, raw Do not use substantial amounts of chain-transferring agent during product, eliminate the process of distillation low-carbon alcohols chain-transferring agent.But institute in polymerization process Relatively low by the mass concentration of monomer, utilization rate of equipment and installations is the highest, and the charge density of polymerizate is relatively low, at high hardness water In, dispersion effect is general.
Acrylates series low polymer is disclosed in JP 56-55407 (the open Application Publication of Japan) Preparation method, due to the introducing of sulfo group in molecule, charge density and the charge density of product the most substantially increase, and make the dispersion of product Property and sequestering power are all greatly improved.But the monomer used by the method is the solution system of acrylates, works as reactant Being excessive concentration, viscosity is significantly raised, reacts wayward, it requires that monomer concentration is relatively low, manufactures relatively inefficient.
Patent CN1367200A describes one with acrylic acid maleic acid (acid anhydride) polymer and sodium silicate warp in aqueous Cross polyreaction, the silicic acid of the silylation with surface activity of formation, sodium silicate, acrylic acid-maleic anhydride copolymer (or third Olefin(e) acid homopolymer) the complex of sodium salt.Product high adsorption capacity, good dispersion, calcium ions and magnesium ions is had preferable exchange capacity And the performance of anti-reprecipitation.Although product property is preferable, but similar to above two kind polymerizate, polymerizate water content The biggest, follow-up distillation processes and remains a need for expending substantial amounts of energy.
Compared to conventional detergent dispersant sodium polyacrylate, in comb-shaped polymer, the existence of carboxylic acid chain ensure that polymer can Must adsorb in solid particles surface with preferable；In side chain, the introducing of the group such as longer oxyethyl chain, makes polymer branching degree carry Height, Polymer adsorption is after the surface of solids, and oxyethyl chain makes sterically hindered enhancing, and the dispersion stabilization of product can be made to carry High；And the introducing of some hydrophobic group has a plurality of advantages: first hydrophobic group introduces, make product have certain surface activity, The degree of branching of product improves, and gives the dispersive property that polymerizate is certain；The introducing of the most appropriate hydrophobic group can be to product Water solublity play certain regulation effect, in aqueous emulsion building-up process, the solid content of product can be made to improve；Additionally, Super-concentrated detergent adds this type of with hydrophobic comb-shaped polymer, hydrophobic group is inserted into the surface activity of ball-type layered liquid crystal Between agent, hydrophilic group is then in the outside of layered liquid crystal so that hydrophilic group not only has osmosis, also has sterically hindered work With, make detergent system more stable.By controlling reaction condition, the molecular weight of regulation and control comb polymers and monomer ratio, obtain Suitably polymerizate.It is contemplated that this type of comb-shaped polymer is added in detergent, the dispersion effect that can play.
Summary of the invention
It is an object of the invention to overcome existing technological deficiency, it is provided that one is green, energy-conservation, water solublity is moderate, solid content High combed macromolecule dispersing agent and preparation method.
The synthesis path of the present invention is as follows:
Wherein, m is the integer of 10 to 20, R1、R3、R4For H or methyl, R2For C4-C12Alkyl, a, b, c are more than zero Integer.
Described combed macromolecule dispersing agent is prepared as steps described below:
(1) by the mix monomer of 1/3 volume, emulsifying agent, chain-transferring agent, initiator, distilled water mixes, and stirs, is warming up to 65-80 DEG C, starting to drip remaining mix monomer after reacting about 1h, 40min-60min drips off, and continues insulation reaction 4-6 hour；
(2) stop heating, be cooled to room temperature, remove upper aqueous layer, obtain combed macromolecule dispersing agent.
As it has been described above, each quality of material consists of: mix monomer 10%-40%, emulsifying agent 0.4%-2%, initiator 1%-3%, chain-transferring agent 2%-4%, distilled water 51%-85%, described polymerization temperature is 65-80 DEG C, reacts easily controllable, no Easily there is implode.
Described mix monomer is by A1、A2And A3Composition, wherein A1Accounting for mix monomer mass fraction is 20%-50%, A2Account for mixed Closing monomer mass mark is 20-50%, A3Accounting for mix monomer mass fraction is 20%-40%.
Described A1、A2And A3The structure of composition is as follows:
Described emulsifying agent is anion surfactant and nonionic surfactant Compositional type emulsifying agent, wherein anion Surfactant and nonionic surfactant mass ratio are 1:4-5:1, preferably 1:2-2:1.In anion surfactant One or more in alkyl sodium sulfate, sodium alkyl benzene sulfonate, MES (MES), nonionic surfactant For one or more in glycosyl amide modified polysiloxane, acetylenic glycols b-oxide polyethers modified siloxane altogether.
Described initiator is persulfate, one or more in water-soluble azo initiator.Persulfate is persulfuric acid Sodium, Ammonium persulfate. etc.；Water-soluble azo initiator is azo-bis-isobutyrate hydrochloride, azo two isobutyl imidazoline hydrochloride etc..
Described chain-transferring agent be isopropanol, mercaptoalcohol, bisulfites one or more.
In combed macromolecule dispersing agent of the present invention synthesizes, the amount of monomer ratio, initiator and chain-transferring agent can Select according to actual needs.
The method provided according to the present invention, is had by the combed macromolecule dispersing agent of radical polymerization gained and is difficult to cruelly The advantage poly-, product is easily isolated, solid content is high.
The combed macromolecule dispersing agent that the present invention provides, has high dispersibility to solid particle.As washing point Powder uses, and crystal grain can be made to suspend in water, and makes crystal reduce at the deposition of fiber surface, and the anti-ability that hardens improves, Detergent industry has potential using value.
The present invention has the advantage that compared with existing synthetic method
(1) present invention adopts water as solvent, and synthetic method is simple, and technique is the most green；
(2) present invention uses emulsion polymerization resulting polymers emulsion water solublity moderate, can be with water natural separation, solid content Height, saves the dewatering process of complexity, power consumption, more energy-conservation；
(3) gained combed macromolecule dispersing agent of the present invention is big to the dispersion amount of solid particle, and dispersion stabilization is good.
Accompanying drawing explanation
Fig. 1 be the embodiment of the present invention 1 synthetic product 1# infrared spectrogram；
Fig. 2 is four embodiments of the present invention, and gained synthetic product is to CaCO3Fineness of dispersion and scattergram；
Fig. 3 is the embodiment of the present invention 1, gained synthetic product dispersion CaCO3Transmission electron microscope picture.
Fig. 4 is the embodiment of the present invention 2, gained synthetic product dispersion CaCO3Transmission electron microscope picture.
Fig. 5 is the embodiment of the present invention 3, gained synthetic product dispersion CaCO3Transmission electron microscope picture.
Fig. 6 is the embodiment of the present invention 4, gained synthetic product dispersion CaCO3Transmission electron microscope picture.
Detailed description of the invention
Hereinafter enumerate instantiation patent of the present invention is illustrated, but the present invention is not limited in following example.
The dispersive property method of testing of embodiment of the present invention gained combed macromolecule dispersing agent, mainly by CaCO3 Dispersion amount and Stability Determination, assay method is as follows:
Weigh 1g polymer salt product, be dissolved in 100ml tool plug graduated cylinder, weigh 2g CaCO3Powder, the most acutely shakes Swing 100 times, stand 30min in room temperature, at 50mL, pipette 20mL dispersion liquid in conical flask, add 65mL water, 10mL 1moL/L HCl solution, mark drop with the NaOH of 0.5mol/L fixed.
Dispersion amount=100.09C (V0-V1)/(2m × 20%)
In formula, the mark liquid concentration of C NaOH；
The quality of m polymer sample；
V0The mark liquid that titration blank consumes is long-pending (mL)；
V1The mark liquid that titration sample consumes is long-pending (mL).
Calculating gained unit is mg/g, and acquired results is the biggest, illustrates that polymer is the biggest to the dispersion amount of granule.
CaCO3Fineness of dispersion and measure of spread thereof: use Particle Size Analyzer that the dispersion after stablizing three days is carried out grain Degree and distribution tests.
CaCO3Dispersion particle diameter distribution straight looks: use transmission electron microscope TEM that the dispersion after stablizing three days is carried out pattern Observe.
Embodiment 1
Monomer used is A1: acrylic acid, A2: Isooctyl acrylate monomer, A3: the degree of polymerization is the methoxypolyethylene glycol methyl-prop of 20 Olefin(e) acid ester, wherein A1: A2: A3=3:1:6, other material consumption, reaction condition and preparation process are as follows:
By methoxypolyethylene glycol methacrylate, 2g that 12g acrylic acid, 4g Isooctyl acrylate monomer, the 24g degree of polymerization are 20 Isopropanol, 1.6g azo two 2,2-Dimethylaziridine hydrochloric acid sodium, 0.2g sodium lauryl sulphate, 0.4g Fructus Vitis viniferae amide modifications aminoethylaminopropyl Polysiloxanes mixes, and finally supplies 100g with water, and stirring and emulsifying is not stratified.Equipped with agitator, return duct, four mouthfuls of thermometer Flask adds the mix monomer emulsion of 1/3 volume, stirs, be warming up to 70 DEG C, start after reaction 1h to drip remaining monomer breast Liquid, about 53min drip off, and continue insulation reaction 4 hours, stopped reaction, remove water layer and i.e. can get the comb that solid content is 50.94% Type macromolecule dispersing agent (1#).
Embodiment 2
Monomer used is A1: methacrylic acid, A2: N-Hexyl methacrylate, A3: the degree of polymerization is the methoxypolyethylene glycol of 19 Acrylate, wherein A1: A2: A3=3:4:3, other material consumption, reaction condition and preparation process are as follows:
By the methoxypolyethylene glycol acrylic acid that 12g methacrylic acid, 16g N-Hexyl methacrylate, the 12g degree of polymerization are 19 Ester, 3.2g sodium sulfite, 1.2g potassium peroxydisulfate, 1g dodecylbenzene sodium sulfonate, 1g butynediols monosubstituted ethoxy ether polyethers change Property siloxanes mixing, finally supply 100g with water, stirring and emulsifying is not stratified.Equipped with agitator, return duct, four mouthfuls of thermometer Flask adds the mix monomer emulsion of 1/3 volume, stirs, be warming up to 80 DEG C, start after reaction 1h to drip remaining monomer breast Liquid, about 40min drip off, and continue insulation reaction 6 hours, stopped reaction, remove water layer and i.e. can get the comb that solid content is 61.25% Type macromolecule dispersing agent (2#).
Embodiment 3
Monomer used is A1: acrylic acid, A2: first butyl acrylate, A3: the degree of polymerization is the methoxypolyethylene glycol methyl-prop of 16 Olefin(e) acid ester, wherein A1: A2: A3=3:3:4, other material consumption, reaction condition and preparation process are as follows:
By methoxypolyethylene glycol methacrylate that 9g acrylic acid, 9g first butyl acrylate, the 12g degree of polymerization are 16, The 2 mercapto ethanol of 3.2g, 1.2g ammonium persulfate solution, 0.5g dodecylbenzene sodium sulfonate, 1g butynediols dipropoxy ether are poly- Ether modified siloxane mixing altogether, finally supplies 100g with water, and stirring and emulsifying is not stratified.Equipped with agitator, return duct, thermometer Four-hole boiling flask in add the mix monomer emulsion of 1/3 volume, stir, be warming up to 80 DEG C, start to drip remaining after reaction 1h Monomer emulsions, about 1h drip off, and continue insulation reaction 5 hours, stopped reaction, and removing water layer and i.e. can get solid content is 44.69% Combed macromolecule dispersing agent (3#).
Embodiment 4
Monomer used is A1: methacrylic acid, and A2: N-Hexyl methacrylate, A3: the degree of polymerization is the methoxypolyethylene glycol of 12 Acrylate, wherein A1:A2:A3=3:1:6, other material consumption, reaction condition and preparation process are as follows:
By methoxypolyethylene glycol acrylate that 12g methacrylic acid, 4g N-Hexyl methacrylate, the 24g degree of polymerization are 12, Isopropanol and mercaptoalcohol are the potassium peroxydisulfate of 1.6g, 1.2g, 0.5g dodecylbenzene sodium sulfonate, 1g butynediols monosubstituted ethoxy Ether polyether modified siloxane mixes, and finally supplies 100g with water, and stirring and emulsifying is not stratified.Equipped with agitator, return duct, temperature The four-hole boiling flask of meter adds the mix monomer emulsion of 1/3 volume, stirs, be warming up to 75 DEG C, start dropping after reacting about 1h surplus Remaining monomer emulsions, about 50min drips off, and continues insulation reaction 6 hours, stopped reaction, and removal water layer i.e. can get solid content and is The combed macromolecule dispersing agent (4#) of 57.25%.
Polymer product structural characterization and Evaluation results thereof that the present invention provides are as follows:
(1) infrared spectrogram of products therefrom 1#, wherein 3419cm during Fig. 1 is embodiment 1-1For carboxylate radical absworption peak, 2931cm-1For CH2Absworption peak, 1710cm-1For the characteristic absorption peak of C=O, at 1650cm-1Without absworption peak, illustrate that monomer is Complete through fundamental reaction.
(2) dispersion amount of gained is recorded for Wei not 1633.52mg/g, 1397.07mg/g and 1382.25mg/ by titration G, 1189.26mg/g correspond to CaCO3Dispersion particle diameter, is respectively the particle size distribution of 1#-4#, it can be seen that mainly collect from Fig. 2 In near 1um, and narrow distribution, illustrate that the comb-shaped polymer of synthesis is to solid particle CaCO3There is good dispersion effect And dispersion stabilization.
(3) the TEM figure of Fig. 3-6 can be seen that CaCO3Particle diameter relatively small, be concentrated mainly on 100 nanometers, and distribution be all Even.

Claims (15)

1. a combed macromolecule dispersing agent, it is characterised in that structural formula is as follows:
Wherein, m is the integer of 10 to 20, R1、R3、R4For H or methyl, R2For C4-C12Alkyl, a, b, c are the integer more than zero.
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 1, it is characterised in that comprise the steps:
(1) by the mix monomer of 1/3 volume, emulsifying agent, chain-transferring agent, initiator, distilled water mixes, and stirs, is warming up to 65-80 DEG C, starting after reacting about 1h to drip remaining mix monomer, 40-60min drips off, and continues insulation reaction 4-6 hour；
(2) stop heating, be cooled to room temperature, remove upper aqueous layer, obtain combed macromolecule dispersing agent.
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 2, it is characterised in that each quality of material group Become: mix monomer 10%-40%, emulsifying agent 0.4%-2%, initiator 1%-3%, chain-transferring agent 2%-4%, distilled water 51%-85%.
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 2, it is characterised in that described mix monomer By A1、A2And A3Composition, wherein A1Accounting for mix monomer mass fraction is 20%-50%, A2Accounting for mix monomer mass fraction is 20- 50%, A3Accounting for mix monomer mass fraction is 20%-40%.
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 4, it is characterised in that described A1Structure such as Under:
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 4, it is characterised in that described A2Structure such as Under:
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 4, it is characterised in that described A3Structure such as Under:
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 2, it is characterised in that described emulsifying agent is The Compositional type emulsifying agent of anion surfactant and nonionic surfactant, wherein anion surfactant and nonionic Surfactant qualities is than for 1:4-5:1.
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 8, it is characterised in that described anion table Face activating agent and nonionic surfactant ratio are 1:2-2:1.
The preparation method of a kind of combed macromolecule dispersing agent the most as claimed in claim 8, it is characterised in that anionic surface is lived Property agent is one or more in alkyl sodium sulfate, sodium alkyl benzene sulfonate, MES.
The preparation method of 11. a kind of combed macromolecule dispersing agents as claimed in claim 8, it is characterised in that non-ionic surface is lived Property agent be one or more in glycosyl amide modified polysiloxane, acetylenic glycols b-oxide polyethers altogether modified siloxane.
The preparation method of 12. a kind of combed macromolecule dispersing agents as claimed in claim 2, it is characterised in that described initiator is Persulfate, one or more in water-soluble azo initiator.
The preparation method of 13. a kind of combed macromolecule dispersing agents as claimed in claim 12, it is characterised in that described persulfuric acid Salt is sodium peroxydisulfate or Ammonium persulfate..
The preparation method of 14. a kind of combed macromolecule dispersing agents as claimed in claim 12, it is characterised in that described water solublity Azo initiator is azo-bis-isobutyrate hydrochloride or azo two isobutyl imidazoline hydrochloride.
The preparation method of 15. a kind of combed macromolecule dispersing agents as claimed in claim 2, it is characterised in that described chain-transferring agent For isopropanol, mercaptoalcohol, bisulfites one or more.
CN201610347276.6A 2016-05-24 2016-05-24 Comb type macromolecular dispersant and preparation method thereof Pending CN106008848A (en)

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CN115466964A (en) * 2022-09-15 2022-12-13 杭州和韵科技有限公司 All-in-one cleaning agent for aluminum and aluminum alloy precision parts and application thereof
CN116239718A (en) * 2023-02-01 2023-06-09 珠海传美讯新材料股份有限公司 Acrylic ester dispersing agent and hot-stamping white ink containing same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115466964A (en) * 2022-09-15 2022-12-13 杭州和韵科技有限公司 All-in-one cleaning agent for aluminum and aluminum alloy precision parts and application thereof
CN116239718A (en) * 2023-02-01 2023-06-09 珠海传美讯新材料股份有限公司 Acrylic ester dispersing agent and hot-stamping white ink containing same

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Application publication date: 20161012