CN115043985B - Series agent for core-shell structure water-based paint and preparation method and application thereof - Google Patents
Series agent for core-shell structure water-based paint and preparation method and application thereof Download PDFInfo
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- CN115043985B CN115043985B CN202210790178.5A CN202210790178A CN115043985B CN 115043985 B CN115043985 B CN 115043985B CN 202210790178 A CN202210790178 A CN 202210790178A CN 115043985 B CN115043985 B CN 115043985B
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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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/02—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of acids, salts or anhydrides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses a core-shell structure water-based paint series agent, a preparation method and application thereof, wherein the series agent has a structure shown in a formula I. The preparation method comprises the following steps: 1) Preparing isosorbide-terminated acrylic acid; 2) Preparation of polyacrylic resins having isosorbide structure in the branched chain. The branched chain isosorbide-containing serial agent prepared by the invention can be effectively applied to water-based paint with a core-shell structure, and can effectively improve the durability and the corrosion resistance of the paint.
Description
[ field of technology ]
The invention relates to the field of water-based paint, in particular to a core-shell structure water-based paint series agent, a preparation method and application thereof.
[ background Art ]
The current domestic water paint market continues to expand to gradually replace oily paint. In terms of environmental friendliness, the water-based paint is beneficial to the healthy development of the environment from raw material sources and in the life cycle from production to use. Aiming at research analysis and prospect of several application fields, the water-based paint has wide prospect in the domestic market at present, but a series of problems still exist.
In the whole, the paint industry will develop towards water-based, powdering and high-solid pulverization, and the environment-friendly policy that is becoming stricter is faced, so that the paint is rapidly transformed and developed around environment-friendly products such as water-based paint, and the water-based paint will be greatly developed. Although the water-based paint achieves outstanding achievement at present, certain difficulty exists in achieving the performance of the solvent-based paint, innovative thinking is utilized to develop high-performance products at present, market competitiveness is improved, and rapid, healthy and orderly development of the water-based environment-friendly paint is promoted.
[ invention ]
The invention mainly solves the technical problem of providing the core-shell structure water-based paint series agent, and the preparation method and the application thereof, which can be used for water-based paint with a core-shell structure and can effectively improve the durability and the anti-corrosion performance of the paint.
In order to solve the technical problems, the invention adopts a technical scheme that:
a core-shell structure water paint series agent is a polyacrylic resin with branched chain containing isosorbide structure, the structure is shown in formula I,
wherein R is 1 Alkoxy or hydroxy of C1-20, R 2 Is H or CH 3 N is between 10 and 200, and m is between 200 and 2000.
In a preferred embodiment of the present invention, a branched isosorbide structure-containing polyacrylic resin is synthesized from isosorbide-terminated acrylic acid and acrylic monomers.
The isosorbide-terminated acrylic acid in a preferred embodiment of the invention has the structure shown in formula II,
the preparation method of the isosorbide-terminated acrylic acid is that the acrylic acid is obtained by dissolving the acryloyl chloride and the isosorbide in tetrahydrofuran according to the ratio of 1:1 and reacting for 4 hours at the temperature of 40-60 ℃.
The acrylic monomer in a preferred embodiment of the present invention is one or more of acrylic acid, methyl acrylate, methacrylic acid, butyl methacrylate, butyl acrylate, methyl methacrylate, hydroxypropyl methacrylate, hydroxyethyl methacrylate, lauryl acrylate, isobornyl methacrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, epoxyacrylate, 1, 6-hexanediol diacrylate, diethylene glycol diacrylate or homologues thereof.
The invention also provides a preparation method of the core-shell structure water-based paint series agent, which comprises the following steps:
(1) Placing an initiator and an acrylic monomer into a reaction container by adopting a living polymerization method, heating to 40-100 ℃ and reacting for 1-6h;
(2) And (3) circularly adding the isosorbide-terminated acrylic acid and acrylic monomer into the system in a sectional feeding mode, wherein the polymerization degree of the core-shell structure water-based paint serial agent obtained through feeding control is between 200 and 2000.
In a preferred embodiment of the present invention, the living polymerization method used in step (1) is one of Atom Transfer Radical Polymerization (ATRP), coordination polymerization, reversible addition-fragmentation chain transfer polymerization (RAFT).
In a preferred embodiment of the invention, in step (1), the molar ratio of the initiator to acrylic monomer is from 1:10 to 200; the initiator is alpha-halogenated alkane, benzyl halide, thiocarbonyl reagent, ziegler-Natta catalyst, pi allyl transition metal type catalyst, alkyl lithium initiator or metallocene initiator; the alpha-halogenated alkane and benzyl halide are required to be used together with a ligand, wherein the ligand is CuCl, cuBr or CuI, bipyridine, tetramethyl ethylenediamine or pentamethyl diethylenetriamine and the like according to the mass ratio of 1:1, mixing and using; the thiocarbonyl reagent is required to be mixed with azodiisobutyronitrile or benzoyl peroxide according to the mass ratio of 1:1.
In a preferred embodiment of the invention, in step (2), the molar ratio of the single charge of isosorbide-terminated acrylic acid to initiator is 1:1; the molar ratio of the single feeding amount of the acrylic monomer to the initiator is 10-200:1.
In a preferred embodiment of the invention, the degree of polymerization of the mobile molecular chains of the tandem agent is in the range of 200 to 2000.
The invention also provides application of the core-shell structure water-based paint series agent in polyacrylic acid and polyurethane core-shell structure water-based paint, wherein the mass ratio of the series agent to the core-shell structure water-based paint is 0.5-5:100.
In summary, due to the adoption of the technical scheme, the beneficial effects of the invention are as follows:
according to the invention, the polyacrylic resin with the branched chain containing the isosorbide structure is synthesized, and the water-based paint with the core-shell structure contains a large number of polar groups, so that the isosorbide structure in the branched chain structure can effectively form a hydrogen bond with the polar groups. The series agent can strengthen acting force between core-shell structures in construction coating, so that the durability and the corrosion resistance of the coating are improved.
[ detailed description ] of the invention
All of the features disclosed in this specification, or all of the steps in a method or process disclosed, may be combined in any combination, except for mutually exclusive features and/or steps.
Any feature disclosed in this specification (including any accompanying claims, abstract) may be provided with respect to each feature disclosed herein, unless otherwise indicated, as an example of a generic series of equivalent or similar features.
Example 1:
the preparation method of the core-shell structure water-based paint series agent comprises the following steps:
(1) Dissolving acryloyl chloride and isosorbide in tetrahydrofuran according to a ratio of 1:1, and reacting at 40 ℃ for 4 hours to obtain isosorbide-terminated acrylic acid for later use;
(2) Adopting an ATRP active polymerization method, taking 1mol of benzyl chloride as an initiator, adopting 1mol of CuBr and 1mol of bipyridine as ligands, adding 20mol of methyl methacrylate into a reaction vessel, heating to 60 ℃, and reacting for 1h;
(3) 1mol of isosorbide-terminated acrylic acid is weighed and added into a reaction system to react for 20min;
(4) Weighing 20mol of methyl methacrylate, adding the methyl methacrylate into a reaction system, and reacting for 1h;
(5) And (3) and (4) are circulated for 10 times, and the core-shell structure water-based paint series agent can be obtained.
10mol of isosorbide-terminated acrylic acid and 220mol of methyl methacrylate are added in the whole preparation scheme, so that the core-shell structure water-based paint series agent formula I can be obtained; in the formula I, R1 is methoxy, R2 is CH 3 N is 20 and m is 230.
The prepared core-shell structure water-based paint series agent and acrylic acid@epoxy paint are mixed according to the mass ratio of 1:100 and then coated on the surface of steel.
The prepared core-shell structure water-based paint series agent and polyurethane@acrylic paint are mixed according to the mass ratio of 1:100 and then coated on the surface of steel.
Example 2:
the preparation method of the core-shell structure water-based paint series agent comprises the following steps:
(1) Dissolving acryloyl chloride and isosorbide in tetrahydrofuran according to a ratio of 1:1, and reacting at 60 ℃ for 4 hours to obtain isosorbide-terminated acrylic acid for later use;
(2) Adding an initiator consisting of 1mol of CuCl and 1mol of bipyridine and 2mol of butyl methacrylate into a reaction vessel by adopting an ATRP active polymerization method, and heating to 75 ℃ for reaction for 1h;
(3) 1mol of isosorbide-terminated acrylic acid is weighed and added into a reaction system to react for 20min;
(4) Weighing 40mol of butyl methacrylate, adding the butyl methacrylate into a reaction system, and reacting for 1h;
(5) And (3) and (4) are circulated for 20 times, and the core-shell structure water-based paint series agent can be obtained.
20mol of isosorbide-terminated acrylic acid and 840mol of butyl methacrylate are added in the whole preparation scheme, so that the core-shell structure water-based paint series agent formula I can be obtained; in the formula I, R1 is butoxy, R2 is CH 3 In formula I, n is 40 and m is 860.
The prepared core-shell structure water-based paint series agent and the acrylic acid@epoxy paint are mixed according to the mass ratio of 0.5:100 and then coated on the surface of steel.
The prepared core-shell structure water-based paint series agent and polyurethane@acrylic paint are mixed according to the mass ratio of 0.5:100 and then coated on the surface of steel.
Example 3:
the preparation method of the core-shell structure water-based paint series agent comprises the following steps:
(1) Dissolving acryloyl chloride and isosorbide in tetrahydrofuran according to a ratio of 1:1, and reacting at 50 ℃ for 4 hours to obtain isosorbide-terminated acrylic acid for later use;
(2) By adopting a RAFT active polymerization method, an initiator adopts 1mol of 2-mercapto-S-thiobenzoyl acetic acid and 1mol of azodiisobutyronitrile, 50mol of acrylic acid and 150mol of methacrylic acid as acrylic monomers, and the mixture is added into a reaction vessel and heated to 60 ℃ for reaction for 6 hours;
(3) 1mol of isosorbide-terminated acrylic acid is weighed and added into a reaction system to react for 20min;
(4) Weighing 50mol of acrylic acid and 150mol of methacrylic acid, adding the acrylic acid and the methacrylic acid into a reaction system, and reacting for 6 hours;
(5) And (3) and (4) are circulated for 8 times, so that the core-shell structure water-based paint series agent can be obtained.
Adding 8mol of isosorbide-terminated acrylic acid and 1800mol of acrylic monomer in the whole preparation scheme, thus obtaining the core-shell structure water-based paint series agent formula I; in the formula I, R1 is hydroxyl, R2 is H and CH 3 In the formula I, n is 200, and m is 1808.
The prepared core-shell structure water-based paint series agent and the acrylic acid@epoxy paint are mixed according to the mass ratio of 5:100 and then coated on the surface of steel.
The prepared core-shell structure water-based paint series agent and polyurethane@acrylic paint are mixed according to the mass ratio of 5:100 and then coated on the surface of steel.
Comparative example 1:
acrylic @ epoxy coating: acrylic acid, methyl methacrylate and styrene were mixed in a ratio of 2:2:1, adding AIBN initiator with the mass fraction of 1% into a reaction system, reacting for 4 hours at 80 ℃, adding epoxy acrylic resin (2.5 times of the mass of the acrylic acid in the previous step), heating to 90 ℃ and reacting for 2 hours to obtain the acrylic acid@epoxy coating. The obtained coating is coated on the surface of steel. The acrylic @ epoxy coatings of examples 1-3 were prepared in the same manner as described.
Polyurethane @ acrylic coating: the hexanediol and diisocyanate were added in a ratio of 1.2:1 to an aqueous solution containing OP-10 with a mass fraction of 2% at 80℃for 2h, after which 5% by mass (calculated as hexanediol) of allyl isocyanate was added for a further 1h. Then, dropwise adding acrylic acid premix (acrylic acid, methyl methacrylate and styrene in a mass ratio of 1:2:1, and adding sodium dodecyl sulfate with a mass fraction of 3 percent) and potassium persulfate with a mass fraction of 1 percent of the acrylic acid premix into the reactants, and reacting for 5 hours at 85 ℃ to obtain the polyurethane@acrylic acid coating. The obtained coating is coated on the surface of steel. The polyurethane @ acrylic coatings of examples 1-3 were prepared in the same manner as described.
The acrylic acid @ epoxy coating and the polyurethane @ acrylic coating prepared in examples 1, 2 and 3 and comparative example 1 were respectively coated on the surfaces of steel materials, and then the following performance tests were performed, and the test results are specifically shown in table 1.
Paint film thickness: the detection is carried out by adopting national standard (GB/T13452.2-2008).
Salt spray resistance: the detection is carried out by adopting national standard (HG/T20720-2020).
Weather resistance: the detection is carried out by adopting national standard (HG/T20720-2020).
The @ is a method for identifying core-shell materials, A@B shows that A is core B and shell
The second row of the table is the name applied to the core-shell coating, the series of agents synthesized in examples 1-3 being added to the core-shell coating.
Table 1 comparison of properties
The series agent provided by the invention can strengthen acting force between core-shell structures in construction coating, so that the durability and the corrosion resistance of the coating are improved.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (10)
1. A core-shell structured water paint series agent is characterized in that the series agent is a polyacrylic resin with branched chain containing isosorbide structure, the structure of the series agent is shown as a formula I,
wherein R1 is alkoxy or hydroxy of C1-20, R2 is H or CH3, n is between 10 and 200, and m is between 200 and 2000.
2. The core-shell structured aqueous coating composition of claim 1, wherein the composition is polymerized from isosorbide-terminated acrylic acid and acrylic monomers.
3. The core-shell structured water-based paint series agent according to claim 2, wherein the isosorbide-terminated acrylic acid has a structure shown in formula II,
4. the core-shell structured aqueous coating composition of claim 3, wherein the isosorbide-terminated acrylic acid is prepared by: the preparation method comprises the steps of dissolving acryloyl chloride and isosorbide in tetrahydrofuran according to a ratio of 1:1, and reacting for 4 hours at 40-60 ℃.
5. The core-shell structured water-based paint series agent according to claim 2, 3 or 4, wherein the acrylic monomer is one or more of acrylic acid, methyl acrylate, methacrylic acid, butyl methacrylate, butyl acrylate, methyl methacrylate, lauryl acrylate or homologs thereof.
6. The method for preparing the core-shell structured water-based paint series agent according to claim 1, comprising the following steps:
(1) Placing an initiator and an acrylic monomer into a reaction container by adopting a living polymerization method, heating to 40-100 ℃ and reacting for 1-6h;
(2) And (3) circularly adding the isosorbide-terminated acrylic acid and acrylic monomer into the system in a sectional feeding mode, and controlling the polymerization degree of the core-shell structure water-based paint series agent to be between 200 and 2000 through feeding.
7. The method according to claim 6, wherein in the step (1), the living polymerization method is one of atom transfer radical polymerization, coordination polymerization, and reversible addition-fragmentation chain transfer polymerization.
8. The process according to claim 6, wherein in step (1), the molar ratio of the initiator to the acrylic monomer is from 1:10 to 200; the initiator is alpha-halogenated alkane, benzyl halide, thiocarbonyl reagent, ziegler-Natta catalyst, pi allyl transition metal type catalyst, alkyl lithium initiator or metallocene initiator; the alpha-halogenated alkane and benzyl halide are needed to be used together with a ligand, wherein the ligand is CuCl, cuBr or CuI and bipyridine, tetramethyl ethylenediamine or pentamethyl diethylenetriamine according to the mass ratio of 1:1, mixing and using; the thiocarbonyl reagent is required to be mixed with azodiisobutyronitrile or benzoyl peroxide according to the mass ratio of 1:1.
9. The process of claim 6, wherein in step (2), the molar ratio of the single charge of isosorbide-capped acrylic acid to initiator is 1:1; the molar ratio of the single feeding amount of the acrylic monomer to the initiator is 10-200:1.
10. The application of the core-shell structure water-based paint series agent according to any one of claims 1-5 in polyacrylic acid and polyurethane core-shell structure water-based paint, wherein the mass ratio of the series agent to the core-shell structure water-based paint is 0.5-5:100.
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