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Study on the synthesis and application of a new type of block polyacrylate hyperdispersant

 Last Update: 2021-11-11
 Source: Internet
 Author: User

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（ARGET-ATRP）A-BA-B-A、，
。（PMDETA），（bBr-iBE）（CuBr2），，
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In the production process of paint and ink, the problem of wetting and dispersing solid pigments in the medium is often involved
.
The wetting and dispersing performance of the pigment in the medium not only affects the production efficiency, energy consumption and raw material consumption of the product, but also affects the final quality of the product, such as gloss, color strength, and tensile strength
.
The wetting and dispersing of pigments is mainly achieved by means of dispersing agents.
Therefore, the synthesis and application of high-efficiency dispersing agents are particularly important
.
In recent years, the synthesis of high-efficiency polymer dispersants has become a hot spot in the study of pigment dispersion aids
.
Polymer dispersants are also called "super dispersants", which have better wetting and dispersing properties than traditional surfactants.
They have been used in actual production, but there are few domestic studies and the products rely on imports
.
Our company mainly researched and developed AB amphiphilic structure hyperdispersants and made detailed application tests on their dispersion properties
.

1.
1 The basic theory of dispersant stability

Since the dispersant is an amphiphilic polymer, the molecular structure is divided into two parts: the anchor end (adsorption part) and the dispersing end (also known as the solvent link), and their mechanism of action is different
.

(1) Anchoring mechanism

The adsorption of the dispersant on the dispersion medium is the prerequisite for its wetting and dispersing performance
.
In non-aqueous systems, the anchoring end generally forms adsorption on the surface of the pigment.
Its interaction with the pigment is related to the type of anchoring group and the surface properties of the particle.
There are four main forms: ion pair (Figure 1A), hydrogen Bond (Figure 1B), surface treatment of dispersed pigments (Figure 1C), chemical adsorption (Figure 1D)

Figure 1: The form of interaction between dispersant and solid surface

(2) Stability mechanism

For the theory of dispersion stability, scholars from various countries have conducted extensive research and proposed different models, including the electric double layer repulsion stability mechanism (DLVO theory), space stability mechanism, and exhaustion stability mechanism
.

1.
2 Molecular structure characteristics of polymer hyperdispersants

The application of traditional dispersants (also known as surfactants) in water dispersion systems is very effective, but there are defects in non-aqueous systems, which are mainly manifested in two aspects: First, traditional dispersants mostly use single-point adsorption In this way, the hydrophilic part cannot form a strong adsorption with the particle surface, and is easy to desorb, which leads to the re-flocculation of the particles; second, the surface charge layer of the particles is compressed, and the contribution of charge stabilization is greatly reduced; while the dispersion end of the traditional dispersant The radical (usually only 8-20 carbon atoms) can not provide enough solvation chain length, which can not provide enough three-dimensional barrier effect for the particles, resulting in the flocculation of dispersed particles
.

The polymer dispersant draws on the basic principles of traditional dispersants and is also an amphiphilic structure.
One end can be adsorbed on the surface of the dispersed particles, and the other end can be dissolved in the dispersion medium to form a three-dimensional barrier to prevent the flocculation of the particles
.
It overcomes the shortcomings of traditional dispersants, not only can introduce multiple adsorption points in each dispersant molecule, but also can freely change the length of the solvation chain by controlling the degree of polymerization
.
Multiple adsorption points simultaneously generate multi-point interactions through hydrogen bonds, covalent bonds, and ionic bonds, which enhance the adhesion between polymer solid particles; proper solvation chain length enables the dispersant to form sufficient three-dimensional on the surface of the solid particles Barrier layer
.
In addition, the macromolecular polymer can only form weak micelles or single-molecule micelles, so it has high fluidity and easily diffuses to the surface of the particles to form an adsorption layer, which increases the wetting efficiency
.
Based on the above characteristics, polymer dispersants have become "hyperdispersants"
.

Polymeric dispersants used in non-aqueous systems are usually block, random, graft copolymers or end group modified homopolymers
.
Their adsorption morphology on the particle surface is shown in Figure 2:

(A) Polymers or block polymers with single-end functional groups (b) Polymers with functional groups at both ends (c) "BAB" type block copolymers (d) "ABA" type block copolymers (e ) Random copolymer (f) Graft or comb copolymer

Figure 2 The adsorption morphology of various polymer dispersants on the solid surface

1.
3 The structure of carbon black and the requirements for dispersant

Commonly used organic pigments are carbon black, including general carbon black and high-pigment carbon black, permanent violet, transparent iron red, phthalopram, organic red and so on
.
The following is the composition of the surface functional groups of carbon black
.

Carbon black is classified as follows according to different blackness:

1) High pigment carbon black: blackness less than 20, particle size (10-16 nm) used in automotive and industrial topcoats;

2) Medium pigment carbon black: blackness 20-32, particle size (16-33 nm);

3) Low-pigment carbon black: blackness 32-45, coarser particle size (33-70 nm), light-colored carbon black is generally blended in car chassis paint, tank enamel and other cheap coatings
.

Blackness is an important indicator for judging the quality of carbon black
.
Blackness is closely related to the specific surface area, structure and surface acidity of the pigment surface .
Carbon black dispersion generally follows the following rules.
The molecular weight of the dispersant will affect the wettability of carbon black particles.
If it is a polymer dispersant, generally speaking: 1) A dispersant with an amino group as an anchor group will make the color paste The viscosity increases, and some even post-thickening; 2) The dispersant that uses polybasic acid as the anchor group will have obvious viscosity reduction effect, so it is the preferred dispersant for dispersing carbon black, such as BYK-163, 161, SOLSPESE 24000 and the like
.

When carbon black is dispersed in the coating system, the blackness of the paint film is mainly affected by the following factors:

1) The type of carbon black, the blue-phase goods are supplemented with light blue and whitening agent;

2) Type of dispersant, generally choose acid-based polymer dispersant;

3) Grinding formula, including the wettability of carrier resin;

4) Grinding equipment, fineness control
.

02Synthesis of hyperdispersant

Hyperdispersants are generally AB type diblock copolymers
.
The anchor section and the solvation section can be synthesized in stages, and then they can be combined by a certain method, or one section is synthesized first, and then it is combined with the monomer of the other section through a certain chemical reaction
.
It is generally realized by methods such as free radical polymerization and condensation polymerization
.
The molecular weight of the dispersant synthesized in this experiment is between 5,000 and 10,000
.

2.
1 Synthesis method

Adopt electron transfer regeneration activator atom transfer radical polymerization, namely ARGET-ATRP controllable radical polymerization principle
.

2.
2 General steps of synthesis:

1) Synthesis of macromolecular initiator bBr-iBE;

2) Synthesize AB and ABA type hydroxyl-containing block polymers;

3) The block polymer is reacted with aminoimidazole to obtain a comb-type polymer hyperdispersant
.

2.
3 Experimental part

(1) Reagents needed for synthesis:

Methyl methacrylate (MMA): Sinopharm reagent, dried with MgSO4 for 1 day before use, distilled under reduced pressure to remove polymerization inhibitor, stored in refrigerator, ready for use; Butyl Acrylate (BuA): Shanghai Chemical Reagent Purchasing Station, processing method Same as above
.
Benzyl methacrylate (BNMA): Hechuang Chemical; Tetrahydrofuran methacrylate (THFMA): Hechuang Chemical; Dimethylaminoethyl acrylate: Sinopharm reagent; Copper bromide (99.
0%): Aladdin reagent; 2-bromide Methyl propionate (98%): Saen Chemical Technology (Shanghai) Co.
, Ltd.
; Acetone: Shanghai Dahe Chemical Industry; N-(3-Dimethylpropyl) Methacrylamide (98%): Shanghai Dibai Chemical Technology Co.
, Ltd.
, N-methylpyrrolidone: Sinopharm reagent; Hydroxyethyl acrylate: Sinopharm reagent, aminoimidazole: Aladdin reagent
.

(2) Synthesis of polymer:

Now only one example is described in detail.
In a 100ML four-necked flask with a thermometer, 36.
16g of BNMA monomer (0.
21mol), 18.
13g of EHA monomer (0.
098mol), and 8.
6g of DMAEA monomer are added.
Prepared initiator bBr-iBE 0.
83g, copper bromide 0.
33g, and 0.
49g PMDETA, add 8ml acetone, mix well, then vacuum and fill with nitrogen, heat up and stir to between 85°C and 90°C, every interval Take samples for ten minutes to test the monomer conversion rate, and use Hangzhou Xuyu liquid chromatograph (WK500) for testing, and gel permeation chromatograph to measure molecular weight and molecular weight distribution
.

(3) Analytical test A WK500 liquid chromatograph manufactured by Hangzhou Xuyu Instrument Analytical Instrument Co.
, Ltd.
was used to test the monomer conversion rate, with acetonitrile as the solvent and methanol as the internal reference
.
The molecular weight and molecular weight distribution of the polymer were tested using a WATERS515 gel permeation chromatograph from Waters Inc.
, the mobile phase was THF, monodisperse polystyrene was the standard sample, the flow rate was 1ML/min, and the test was conducted at room temperature
.

(4) The above polymer is dissolved in xylene, and then reacted with aminoimidazole.
By changing the type and quantity of monomers in the solvent segment, different products are obtained for performance testing, and dispersants suitable for different application systems are obtained.
The paper takes one of the dispersant Anjeka-6510 for performance test comparison
.

03Performance application test

Mainly for carbon black testing.
After screening and selecting common products in the market, BYK163 is a polymer polyurethane dispersant with amino groups as anchoring groups.
It is a widely applicable dispersant launched by BYK in the 1970s.
Disponer 9850 is a polymer dispersant with multiple adsorption groups from Deqian Company, EFKA4047 is a polyurethane dispersant launched by Qiba-EFKA
.

3.
1 Test system:

Hydroxy acrylic resin system, respectively used as automotive middle paint and top coat
.
In the above-mentioned system, the performance evaluation and application test of the color paste and the matching paint used in the solid-color topcoat of organic carbon black and inorganic titanium dioxide pigments have been carried out
.

3.
2 Test materials

HypomerFS-3060: Hydroxy acrylic resin (NV=60%, OH%=3.
0%) Deuchem; FW200: Carbon black Evonik; DisponerDP9850: Wetting and dispersing agent Deuchem; BYK-163: Wetting and dispersing agent BYK; EFKA-4047: Wetting and dispersing agent Wetting and dispersing agent Qiba-EFKA; Anjeka-6510: Wetting and dispersing agent, Anjikang Thinner: Xyl/nBAc/PMAc=4/3/1; N-75: curing agent Bayer
.

3.
3 The test experiment steps are as follows:

1) Test the dispersing performance of several dispersants on carbon black in oily systems
.
At the same time, compare and evaluate the viscosity reduction, foam stabilization, color development and storage stability of Disponer9850, BYK-163, and EFKA-4047;

2) Grind the white slurry and mix the paint, then mix it with the black paint 4:1 to form a multi-color paint, add N-75 curing agent and 10% thinner according to the proportion, stir evenly, use 34# wire rod to scrape the PE film and On white cardboard, put it in an oven at 70°C after the surface is dry, and dry for 30 minutes, compare the color development and color difference (referring to the research method); measure the L, a, b values of the referenced and non-referenced research areas to observe the dispersant Effect and degree of floating

3) Place the black paint on the Red Devil Kuaishou (high-speed dispersing grinder) and oscillate to make it foam.
The vibration frequency of Kuaishou is 10 times per second
.
Then observe its foam stabilization;

4) After two weeks of storage at 50°C, compare the floating and blooming phenomenon after storage
.

3.
4 Test formula

1) 8% black paste formula

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2) Black paint formula

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3) White pulp formula

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Prepare 150g of color paste according to formula 1, add 450g of steel balls (with a weight ratio of 3:1), then use Red Devil to quickly grind the carbon black at high speed, and measure the fineness after every 1h.

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1H, um

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2H, um

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3H, um

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4H, um

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BYK-163

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Deuchen9850

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EFKA-4047

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Anjeka-6510

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Fineness after heating and storage

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1 week, um

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2 weeks, um

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3 weeks, um

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BYK-163

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Deuchen9850

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EFKA-4047

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Anjeka-6510

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The viscosity of the color paste under the same solid content.

Viscosity reduction: FW-200 carbon black

It can be seen from the above table that its viscosity reduction and storage stability have excellent performance
.

3.
5.
2 Anti-floating effect

Use the finger research method to evaluate the color development, the first anti-floating color, the white paint and the black paste are mixed into a multi-color paint according to the pigment content of 100:3, and the film is scraped, and the color development of the paint paste is judged by the finger research evaluation method Sex
.

The test method is to scrape the film with a 34# scraper to determine the hue
.
According to formula two, it is configured into a paint spray board, and the hue is measured
.
Take the unspecified place as the standard value, and measure the color difference after the mark.
The larger the color difference, the more obvious the floating color and the worse the effect of the dispersant
.

Refers to the storage appearance of the research colored paint as follows:

Color difference measurement after spraying of black paste, black paint and multi-color paint:

04 Conclusion

In this thesis, a new type of block copolymer with controllable molecular weight and narrow molecular weight distribution of AB and ABA was synthesized using the principle of electron transfer regeneration activator atom transfer radical polymerization (ARGET-ATRP).
An amine-based compound was used for reactive modification to obtain an ultra-dispersant Anjeka-6510, which mainly passed the application test of black color paste and recolor paint for Yutong automotive topcoats.
Other organic pigments were also tested, which are commonly used in the market.
When comparing the dispersant, the dispersant has excellent effects in reducing viscosity and preparing high-solid and low-viscosity color pastes, and the color paste prepared from it has almost no floating color when it is used in multi-color paint.
Eliminate, and the chromatic aberration is very small
.
Increase the concentration of color paste, shorten the production cycle in production, and improve production efficiency
.
The reduction of viscosity makes the operation more convenient for users
.

references

1.
Zhou Chunlong, Mu Zhenyi edited Organic Pigment Chemistry and Technology, China Petrochemical Press, 1997

2.
Zhang Xueli, Wang Zhengdong, Hu Liming, Chemical Journal of Colleges and Universities, 1997, 18 (4), P637-P641

3.
Edited by the Department of Polymer Science, Fudan University, "Experimental Technology of Polymer Science", Fudan University Press, 1995

4.
Qian Fenglin, Coating Additives edited by Zhu Yushu, Chemical Industry Press, 1999 edition

5.
Yang Qiyue, Paint Industry, 1991,5,52-55

6.
Hong Xiaoyin, edited by Feng Hanbao, Coating Chemistry, Science Press, 1997

7.
(a) Wang Zhengdong, Chen Waqiong, Zhang Jinxiang, Ink, 1999, April, 19-21 (b) Alan Cowley, Dr MikeGoode,.
Additives, 991, 181 (4297), 736-739

8.
US 6506899, Pigment dispersants formed by reacting an isocyanate with a poly(ethylene glycol) alkyl ether, a polyester or polyester or polyacrylate and a diamine; Simms; John A.
(Wilmington, DE); EI du Pont de Nemours and Company (Wilmington, DE)

9.
US 5882393, DispersingAgent, Quednau; Peter Hermann (Hillegom, NL); Pirrung; Frank OliverHeinrich (JTAlkmaar, NL); EFKA Chemicals BV

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