CN110483789A - A kind of amphipathy hyperbranched polymer and application - Google Patents
A kind of amphipathy hyperbranched polymer and application Download PDFInfo
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- C09D17/00—Pigment pastes, e.g. for mixing in paints
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Abstract
The invention belongs to technical field of polymer materials, in particular to a kind of amphipathy hyperbranched polymer and application；The polymer is made of hyperbranched polyether and end of the chain methoxy poly (ethylene glycol) of raw material；The polymer contains carbon ester bond, ammonia ester bond, estersil key, thioester bond, which is suitable for a variety of inorganic pigments, and have efficient absorption property and dispersion stabilization to inorganic pigment for dispersing inorganic filler；Meanwhile the environmental protection type polymer is nontoxic, viscosity is low, dissolubility is good, and the solvent usage in use process is greatly reduced, and reduces organic emission, is conducive to environmental protection.
Description
Technical field
The invention belongs to technical field of polymer materials, in particular to a kind of amphipathy hyperbranched polymer and application.
Background technique
Inorganic pigment is the inorganic material powder colorant containing metallic element, such as copper-chrome black, iron oxide red, titanium yellow, cobalt
Indigo plant, titanium white etc., and there is high temperature resistant, it is weather-proof, the advantages that strong covering power, the every field that is widely used in people's life.But
Inorganic pigment is insoluble in the media such as water, organic solvent, and has high surface energy, and easy to reunite, partial size increases, and pigments system is extremely unstable
It is fixed, seriously affect its practical application, therefore before use, must be surface-treated to inorganic pigment, improve its dispersion performance.
Pigment dispersing agent system steadily disperses certain solid particle in liquid and the functional additive researched and developed.Existing
Have in technology, the research of existing high-molecular dispersant for inorganic pigments, such as 201480049250.2 disclose " inorganic pigment use
Macromolecule dispersing agent ", it is used in non-aqueous solvent, disperses basic mineral pigment, but the performance of macromolecule dispersing agent and answer
With range by significant limitation.For another example 200710024152.5 disclose a kind of " the non-ionic hyperbranched type of organic pigment
The preparation method of macromolecule dispersing agent ", although disclosing hyperbranched polyether and polyethylene glycol, its also need to add coupler,
Solvent, precipitating reagent, the quality of molar ratio and precipitating reagent and deionized water with greater need for strict control coupler and hydrophily chain
Than increasing and realizing difficulty and production cost, and the dispersing agent is served only in organic pigment.For another example 201610739971.7 disclosure
" degradable polyglycol modified ultra-branching polyether ester and preparation method thereof ", although disclose hyperbranched polyether and poly- second two
Alcohol also achieves product by not soluble in water to the transformation for being dissolved in water, overcomes many dissaving polymers that cannot make in water-based system
Disperse bad problem with or water-based system, but secondary pollution is easy to produce using fusion method, and equipment requirement is high.For another example
201810322269.X disclose " a kind of polyethers and the double modified polyethyleneimine aqueous dispersions of carboxylic acid and preparation method thereof with answer
With ", realize aqueous dispersion of the aqueous dispersion applied to inorganic particles such as inorganic pigment, silicon carbon powder and graphenes, but its
In Michael addition reaction method in need to be added dropwise the alpha, beta-unsaturated acid of alpha, beta-unsaturated acid salt and polyethers under stiring
The mixing aqueous of ester, about 0.5~1.5h of time-consuming, cause operation difficulty height, and control requires high.
Therefore, although dissaving polymer has the polymer of highly branched degree, there are highly dissoluble, low viscosity and good
Rheological characteristic, there is a great potentiality in terms of pigment dispersion, but its equipment requirement is high, at high cost, operation difficulty there is still a need for overcoming
The defects of big.
And the storage for depositing inorganic pigment after treatment for the macromolecule dispersing agent of inorganic pigment in the prior art is stablized
Property it is poor, easily occur phenomena such as fading, fall off, desalinating, changing colour, having seriously affected the quality parameter of inorganic pigment.
Summary of the invention
The present invention is in order to solve the above technical problems, provide a kind of amphipathy hyperbranched polymer and application.
It is realized particular by following technical scheme:
The present invention provides a kind of amphipathy hyperbranched polymer, the polymer is by hyperbranched polyether and end of the chain methoxyl group
Polyethylene glycol is made of raw material；The chemical structural formula of the polymer is as follows:
R in formula is alkyl or aromatic ring yl containing C, N, Si or S.
The polymer contains carbon ester bond, ammonia ester bond, estersil key, any one or a few in thioester bond.
The molecular weight of the methoxy poly (ethylene glycol) is 200~200000.
The degree of branching of the hyperbranched polyether is 0.2~0.9.
The amphipathy hyperbranched polymer is the nanoparticle with core-shell structure.
The amphipathy hyperbranched polymer is for dispersing inorganic pigment.
The inorganic pigment is iron oxide red, titanium dioxide, chrome oxide green, iron oxide yellow, cadmium red, zinc yellow, cobalt blue, titanium yellow
In any one.
The present invention also provides the methods that amphipathy hyperbranched polymer is used to disperse inorganic pigment, including step are as follows:
1) pigment and amphipathy hyperbranched polymer 100:(1-8 in mass ratio are weighed), addition stirring solvent is uniform, solvent
Volume ratio with pigment is (20-50): 1；
2) it is dispersed, obtains pigment dispersion system.
The solvent be water, ethyl alcohol, propyl alcohol, butanol, butyl acetate, in propylene glycol methyl ether acetate any one or it is several
Kind mixture.
It is described be separated into ultrasonic wave dispersion or high speed dispersion in it is any.
The operating condition of the ultrasonic wave dispersion: ultrasonic power 700-900W, ultrasonic time 10-40min；It is preferred that
800W。
The operating condition of the high speed: revolving speed is 1500-2000 revs/min, time 10-40min；It is preferred that 1800 revs/min.
The preparation method of the amphipathy hyperbranched polymer:
Using esterification process, specifically: hyperbranched polyether (1) and acid or acid anhydrides or carboxylic acid halides (2) are dissolved in dimethylbenzene or N, N-
Dimethylformamide, under nitrogen protection, 50~100 DEG C are reacted 5~15 hours, are added methoxy poly (ethylene glycol) (mPEG, 3),
Reacted 12~36 hours in 80~150 DEG C, 1,2,3 molar ratio is 5:3:1~1:1:1, after react addition anhydrous ether or
Petroleum ether or n-hexane sedimentation, obtain amphipathy hyperbranched polymer.
The present invention have it is following the utility model has the advantages that
Amphipathy hyperbranched polymer of the invention have highly branched degree polymer, have highly dissoluble, low viscosity and
Good rheological characteristic forms nucleocapsid micella, i.e. nanoscale spherical shape nucleocapsid structure carrier, benefit for dispersing various inorganic pigments
Pigment particles are played with stable peptizaiton with its micro- glue characteristic and steric hindrance, avoids linear macromolecule dispersing agent due to twining
It flocculates caused by phenomenon, there is good dispersion stabilization to inorganic pigment.
Compared with existing dispersing agent, this dispersing agent has the advantage that (1) good mobility；Point of this dispersing agent
Minor structure is different from the structure that traditional line polymer is easily wound, and molecular structure has three-dimensional structure in space, point
Substantially there is no branch chain entanglement between son, bridge effect will not occur for coated pigment, to show preferable Newtonian fluid row
For；(2) good stability；It will be applied to the carrier of adsorption pigment with this dispersing agent of nucleocapsid structure, utilize its micro- Jiao Te
Property and steric hindrance pigment particles are played with the peptizaiton of anchorage mechanism, so that dispersion is kept lesser partial size, avoid
Linear macromolecule dispersing agent is flocculated phenomenon due to caused by winding, to maintain the dispersity of pigment stabilizer；Such as Fig. 1 institute
Show, the mechanism of action of linear polymeric dispersing agent and amphipathy hyperbranched polymer dispersing agent of the present invention and inorganic pigment is carried out
Signal.
The present invention passes through contained in the degree of branching of strict control polymer, the molecular weight and chain of end of the chain methoxy poly (ethylene glycol)
Functional group, obtain the amphiphilic superbranched polyether with multiple property, compatibility is good, be applicable to a variety of inorganic pigments,
And the nanoparticle with core-shell structure can be self-assembled into；Had efficiently based on each anchoring end group to different inorganic pigment particles
Absorption property, nanoscale spherical shape nucleocapsid structure carrier can be formed in different media, utilize its micro- glue characteristic and space bit
Stable peptizaiton is played in resistance to pigment particles, can effectively improve the dispersion stabilization of pigment, and linear macromolecule is avoided to disperse
Agent is flocculated phenomenon due to caused by winding.
Amphipathy hyperbranched polymer of the invention is environment-protecting and non-poisonous, its viscosity is low in addition, dissolubility is good, and can be greatly decreased makes
With solvent usage in the process, waste discharge is reduced, environmental protection is conducive to.
The invention is simple and feasible, environment friendly and pollution-free, is suitable for industrialized production, and market application prospect is optimistic.
Detailed description of the invention
Fig. 1 is the peptizaiton machine that amphipathy hyperbranched polymer pigment dispersing agent provided by the invention disperses inorganic pigment
Reason；
Fig. 2 be amphipathy hyperbranched polymer dispersion pigment transmission electron microscope figure (left figure be in 1 pigment of embodiment
Transmission electron microscope figure in dispersion, right figure are the transmission electron microscope in 6 pigment dispersion system of embodiment
Figure)；
Fig. 3 is scanning electron microscope diagram of the amphipathy hyperbranched polymer provided by the invention to pigment before and after the processing；
Fig. 4 is iron oxide red, titanium dioxide, chrome oxide green, iron oxide yellow, cadmium red, zinc yellow, cobalt blue, the dispersion force of titanium yellow
(1-8 is iron oxide red, titanium dioxide, chrome oxide green, iron oxide yellow, cadmium red, zinc yellow, cobalt blue, titanium yellow respectively to comparison diagram in figure
Label；Ordinate is dispersion force, unit %).
Specific embodiment
Specific embodiments of the present invention will be described in further detail below, but the invention is not limited to these realities
Mode is applied, it is claimed to still fall within the claims in the present invention for any improvement or replacement on the present embodiment essence spirit
Range.
The amphipathy hyperbranched polymer that embodiment 1-10 is provided, the polymer is by hyperbranched polyether and end of the chain methoxyl group
Polyethylene glycol is made of raw material；The polymer contains carbon ester bond, ammonia ester bond, estersil key, thioester bond；The chemistry knot of the polymer
Structure formula is as follows:
R in formula is alkyl or aromatic ring yl containing C, N, Si or S；
Embodiment 1
Amphipathy hyperbranched polymer is present embodiments provided for dispersing the method for inorganic pigment, including step are as follows:
1) pigment and amphipathy hyperbranched polymer 100:2 in mass ratio are weighed, is taken water as a solvent, it is equal that stirring solvent is added
Even, the volume ratio of solvent and pigment is 50:1, and wherein the degree of branching of the hyperbranched polyether of amphipathy hyperbranched polymer is 0.47,
The molecular weight of methoxy poly (ethylene glycol) is 2000；
2) disperse through ultrasonic wave, obtain pigment dispersion system；
The operating condition of the ultrasonic wave dispersion: ultrasonic power 800W, ultrasonic time 20min；
Tem study is carried out to pigment dispersion system, as the result is shown: amphipathy hyperbranched polymer can
Self assembly forms the nanoparticle with core-shell structure, such as the left figure in Fig. 2.
Embodiment 2
Difference from example 1 is that: solvent is ethyl alcohol.
Embodiment 3
Difference from example 1 is that；Solvent is propyl alcohol.
Embodiment 4
Difference from example 1 is that: solvent is butanol.
Embodiment 5
Difference from example 1 is that: solvent is water, ethyl alcohol, propyl alcohol, butanol by isometric composition.
Embodiment 6
Amphipathy hyperbranched polymer is present embodiments provided for dispersing the method for inorganic pigment, including step are as follows:
1) pigment and amphipathy hyperbranched polymer 100:6 in mass ratio are weighed, using butyl acetate as solvent, solvent is added
It stirs evenly, the volume ratio of solvent and pigment is 20:1, wherein the degree of branching of the hyperbranched polyether of amphipathy hyperbranched polymer
It is 0.51, the molecular weight of methoxy poly (ethylene glycol) is 5000；
2) through high speed dispersion, pigment dispersion system is obtained；
The operating condition of the high speed: revolving speed is 1800 revs/min, time 30min；
Tem study is carried out to pigment dispersion system, as the result is shown: amphipathy hyperbranched polymer can
Self assembly forms the nanoparticle with core-shell structure, such as the right figure in Fig. 2.
Embodiment 7
With embodiment 6 the difference is that: solvent is propylene glycol methyl ether acetate.
Embodiment 8
With embodiment 6 the difference is that: solvent is butanol.
Embodiment 9
With embodiment 6 the difference is that: solvent is ethyl alcohol and butyl acetate by isometric composition.
Embodiment 10
With embodiment 6 the difference is that: solvent be butyl acetate, propylene glycol methyl ether acetate, butanol, ethyl alcohol by etc.
Volume composition.
Embodiment 11
The preparation method of the amphipathy hyperbranched polymer:
Hyperbranched polyether (1) and acid or acid anhydrides or carboxylic acid halides (2) are dissolved in dimethylbenzene or n,N-Dimethylformamide, in nitrogen
Under protection, 50 DEG C are reacted 5 hours, are added methoxy poly (ethylene glycol) (mPEG, 3), are reacted 12 hours in 800 DEG C, 1,2,3 mole
Than anhydrous ether or petroleum ether or n-hexane sedimentation are added after for 5:3:1, having reacted, amphipathy hyperbranched polymer is obtained.
Embodiment 12
Using esterification process, specifically: hyperbranched polyether (1) and acid or acid anhydrides or carboxylic acid halides (2) are dissolved in dimethylbenzene or N, N-
Dimethylformamide, under nitrogen protection, 100 DEG C are reacted 15 hours, are added methoxy poly (ethylene glycol) (mPEG, 3), in 150 DEG C
Reaction 36 hours, 1,2,3 molar ratio are 1:1:1, and anhydrous ether or petroleum ether or n-hexane sedimentation are added after having reacted, obtains
Amphipathy hyperbranched polymer.
Embodiment 13
Present embodiments provide the preparation method of amphipathy hyperbranched polymer:
Hyperbranched polyether (1) and acid or acid anhydrides or carboxylic acid halides (2) are dissolved in dimethylbenzene or n,N-Dimethylformamide, in nitrogen
Under protection, 80 DEG C of reaction 10h are added methoxy poly (ethylene glycol) (mPEG, 3), and for 24 hours in 100 DEG C of reactions, 1,2,3 molar ratio is
1:1:1 is added anhydrous ether sedimentation, obtains amphipathy hyperbranched polymer after having reacted.
Embodiment 14
The preparation method of the amphipathy hyperbranched polymer:
Using esterification process, specifically: hyperbranched polyether (1) and acid or acid anhydrides or carboxylic acid halides (2) are dissolved in dimethylbenzene or N, N-
Dimethylformamide, under nitrogen protection, 75 DEG C are reacted 10 hours, are added methoxy poly (ethylene glycol) (mPEG, 3), anti-in 115 DEG C
It answers 24 hours, 1,2,3 molar ratio is 2:1:1, and anhydrous ether or petroleum ether or n-hexane sedimentation are added after having reacted, obtains two
Parent's property dissaving polymer.
Comparative example 1
Difference from example 1 is that: it is substituted using polyethers and the double modified polyethyleneimine aqueous dispersions of carboxylic acid
Amphipathy hyperbranched polymer, simultaneous with polyether lateral chain and lateral carboxylate group on the polyethyleneimine strand of the dispersing agent.
Comparative example 2
With embodiment 6 the difference is that: amphiphilic hyper-branched polymerize using the carboxylate substitution of ultra-branching polyether ester
Object.
Test example 1
The resulting pigment dispersion mechanical energy dispersion performance of embodiment and comparative example is measured, wherein pigment is iron oxide
Red, dispersion force is calculated according to sedimentation, and pigment particle size is measured using nano-particle size analysis instrument, and viscosity is measured using viscosmeter；Knot
Fruit is as shown in table 1:
Table 1
| Dispersion force (%) | Pigment particle size (μm) | Viscosity (mPas) | |
| Embodiment 1 | 95~70 | 1.50~5.10 | 1.85~4.01 |
| Embodiment 2 | 93~80 | 1.80~6.30 | 1.92~4.15 |
| Embodiment 3 | 93~85 | 1.95~6.02 | 2.05~4.20 |
| Embodiment 4 | 93~68 | 2.02~6.50 | 2.54~5.35 |
| Embodiment 5 | 98~78 | 1.35~4.65 | 1.90~5.25 |
| Embodiment 6 | 93~68 | 3.80~10.80 | 3.15~7.20 |
| Embodiment 7 | 93~69 | 2.10~12.36 | 4.03~6.98 |
| Embodiment 8 | 95~79 | 1.75~10.02 | 3.01~7.07 |
| Embodiment 9 | 96~68 | 1.68~9.89 | 2.88~4.96 |
| Embodiment 10 | 97~70 | 2.52~7.18 | 2.66~5.55 |
| Comparative example 1 | 82~60 | 5.36~17.20 | 4.80~8.80 |
| Comparative example 2 | 90~63 | 3.96~14.98 | 4.15~7.65 |
Test example 2
The application is in order to probe into amphipathy hyperbranched polymer to the dispersion effect of a variety of inorganic pigments, using embodiment 6
Method iron oxide red, titanium dioxide, chrome oxide green, iron oxide yellow, cadmium red, zinc yellow, cobalt blue, titanium yellow are dispersed respectively,
Then electron-microscopic analysis is scanned to sample, as the result is shown: pigment agglomerates significantly reduce, even particle distribution, pigment
Handle the left and right figure that forward and backward situation is detailed in Fig. 3.
Test example 3
Using the method for embodiment 8 respectively to iron oxide red, titanium dioxide, chrome oxide green, iron oxide yellow, cadmium red, zinc yellow, cobalt
Blue, titanium yellow is dispersed, and then carries out dispersion force measurement to sample, and measurement result is shown: dispersion force size is followed successively by oxidation
Iron oxide red, iron oxide yellow, cobalt blue, zinc yellow, chrome oxide green, titanium dioxide, cadmium red, titanium yellow, as a result as shown in Figure 4.
The above described is only a preferred embodiment of the present invention, not being made any form of restriction to inventing type, appoint
What is to the above embodiments according to the technical essence of the invention any simply to repair without departing from technical solution of the present invention content
Change, equivalent variations and modification, all of which are still within the scope of the technical scheme of the invention.
Claims (10)
1. a kind of amphipathy hyperbranched polymer, which is characterized in that the polymer is gathered by hyperbranched polyether and end of the chain methoxyl group
Ethylene glycol is made of raw material；The chemical structural formula of the polymer is as follows:
2. amphipathy hyperbranched polymer as described in claim 1, which is characterized in that the polymer contains carbon ester bond, urethane
Key, estersil key, any one or a few in thioester bond.
3. amphipathy hyperbranched polymer as described in claim 1, which is characterized in that R in the chemical structural formula be containing C,
N, the alkyl or aromatic ring yl of Si or S.
4. amphipathy hyperbranched polymer as described in claim 1, which is characterized in that the molecule of the methoxy poly (ethylene glycol)
Amount is 200~200000.
5. such as claim 1 or the amphipathy hyperbranched polymer, which is characterized in that the degree of branching of the hyperbranched polyether
It is 0.2~0.9.
6. amphipathy hyperbranched polymer as claimed in claim 1 or 2, which is characterized in that the amphipathy hyperbranched polymer
It is the nanoparticle with core-shell structure.
7. the amphipathy hyperbranched polymer as described in claim any one of 1-6, uses esterification process to be made, feature exists
In specific preparation method: hyperbranched polyether (1) and acid or acid anhydrides or carboxylic acid halides (2) are dissolved in dimethylbenzene or N, N- dimethyl
Formamide, under nitrogen protection, 50~100 DEG C are reacted 5~15 hours, are added methoxy poly (ethylene glycol) (mPEG, 3), in 80~
150 DEG C are reacted 12~36 hours, and 1,2,3 molar ratio is 5:3:1~1:1:1, and anhydrous ether or petroleum ether is added after having reacted
Or n-hexane sedimentation, obtain amphipathy hyperbranched polymer.
8. amphipathy hyperbranched polymer is for dispersing inorganic pigment as described in claim any one of 1-7.
9. the application of amphipathy hyperbranched polymer as claimed in claim 6, which is characterized in that the inorganic pigment is iron oxide
Red, titanium dioxide, chrome oxide green, iron oxide yellow, cadmium red, zinc yellow, cobalt blue, titanium yellow any one.
10. the method that the amphipathy hyperbranched polymer as described in claim 8 or 9 is used to disperse inorganic pigment, including step are as follows:
1) pigment and amphipathy hyperbranched polymer 100:(1-8 in mass ratio are weighed), addition stirring solvent is uniform, solvent and face
The volume ratio of material is (20-50): 1；
2) it is dispersed, obtains pigment dispersion system.
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