CN111393569B - Styrene maleic amide acid copolymer and preparation method thereof - Google Patents
Styrene maleic amide acid copolymer and preparation method thereof Download PDFInfo
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- CN111393569B CN111393569B CN202010263000.6A CN202010263000A CN111393569B CN 111393569 B CN111393569 B CN 111393569B CN 202010263000 A CN202010263000 A CN 202010263000A CN 111393569 B CN111393569 B CN 111393569B
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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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
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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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
- C09D17/006—Metal
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Abstract
The invention relates to the technical field of synthesis of high polymer material auxiliaries, and particularly provides a preparation method of a styrene maleic amic acid copolymer. The first aspect of the present invention provides a method for preparing a styrene maleic amide acid copolymer, which at least comprises the following steps: (1) preparing maleamic acid; (2) preparing a styrene maleic amide acid copolymer; (3) and (5) purifying. The copolymer which has good water solubility and does not react with metal can be prepared, and is particularly suitable for being used as a dispersant of water-soluble metal pigment.
Description
Technical Field
The invention relates to the technical field of synthesis of high polymer material auxiliaries, and particularly provides a styrene maleic amic acid copolymer and a preparation method thereof.
Background
Metallic pigments refer to metals or metal alloys that are ground into powders or flakes. Although the metallic pigment has a special appearance, color and luster, the metallic pigment is easily discolored by chemical reactions such as oxidation during use and has a problem that the dispersion is unstable and sedimentation is easily caused, compared with common organic pigments. At present, acrylic acid copolymer is a relatively common water-soluble resin dispersant, which has a high acid value and can react with ammonium hydroxide to form carboxylic acid ammonium salt to be dissolved in water, and can bring the effects of complete dissolution, limited self-polymerization deposition, small particle size and clear appearance. The solution has good wetting property and is widely applied to organic pigment formulas. Although the ammonium carboxylate has the property of being soluble in water, the stability of the metallic pigment is easily deteriorated when the ammonium carboxylate is applied to the metallic pigment.
To reduce the negative effects of carboxylic acid salts, carboxylic acid groups can be esterified with hydrophilic alcohols, such as ethylene oxide oligomers. Although this method is helpful for surface activity, its nonionic surfactant component has no cationic character, limiting its use. Alternatively, a co-solvent, such as ethanol or ethylene glycol, may be introduced into the system to increase water solubility and aid in the neutralization of the resin. However, these approaches all result in an increase in VOC, which is contrary to the original intention of aqueous formulations. And only the ammonium carboxylate is diluted and no elimination is achieved.
The present invention has been made to solve the above problems, and it is an object of the present invention to provide a styrene maleic amide acid copolymer which can be used as a dispersant for water-soluble metallic pigments, can provide a good dispersion effect, and can maintain the primary color of the metal for a long period of time.
Disclosure of Invention
In order to solve the above technical problems, a first aspect of the present invention provides a method for preparing a styrene maleic amide acid copolymer, comprising at least the steps of:
(1) preparing maleamic acid;
(2) preparing a styrene maleic amide acid copolymer;
(3) and (5) purifying.
As a preferred technical scheme of the invention, the raw materials for preparing the styrene-maleic amide acid copolymer comprise styrene, alkylamine and maleic anhydride.
In a preferred embodiment of the present invention, the molar ratio of styrene to alkylamine to maleic anhydride is (1 to 3): (0.5-2): 1.
as a preferred technical scheme of the invention, the raw materials for preparing the styrene-maleic amide acid copolymer further comprise, by weight, 30-80% of a solvent, 0.1-2% of an initiator, 0.5-5% of a molecular weight regulator, and styrene, alkylamine and maleic anhydride for the balance.
In a preferred embodiment of the present invention, the alkylamine is selected from one or a combination of several of monoalkylamine, dialkylamine, alkyldiamine, alkyltriamine and alkylpolyamine.
In a preferred embodiment of the present invention, the alkylamine has 1 to 8 carbon atoms.
As a preferred technical scheme of the invention, the solvent is selected from one or a combination of a plurality of benzene solvents, ketone solvents and ester solvents.
As a preferable technical scheme of the invention, the initiator is organic peroxide or azo compound.
In a preferred embodiment of the present invention, the molecular weight regulator is an alkyl mercaptan and/or an aromatic compound.
The second aspect of the present invention provides a styrene maleamic acid copolymer prepared according to the preparation method.
Has the advantages that: the invention provides a styrene maleic amide acid copolymer and a preparation method thereof, wherein maleic anhydride is dissolved in a solvent to react with monoalkylamine, especially monomethylamine, and then react with styrene, and the copolymer which has good water solubility and does not react with metal can be prepared by regulating the molar ratio of styrene, alkylamine and maleic anhydride, is particularly suitable for being used as a dispersing agent of water-soluble metal pigment, and can be better applied to the preparation of metal color paste.
Detailed Description
The disclosure may be understood more readily by reference to the following detailed description of preferred embodiments of the invention and the examples included therein. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification, including definitions, will control.
The terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
In addition, the indefinite articles "a" and "an" preceding an element or component of the invention are not intended to limit the number requirement (i.e., the number of occurrences) of the element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component also includes the plural unless the stated number clearly indicates that the singular form is intended.
In order to solve the above technical problems, a first aspect of the present invention provides a method for preparing a styrene maleic amide acid copolymer, comprising at least the steps of:
(1) preparing maleamic acid;
(2) preparing a styrene maleic amide acid copolymer;
(3) and (5) purifying.
In a preferred embodiment, the raw materials for preparing the styrene maleamic acid copolymer include styrene, alkylamine, and maleic anhydride.
In a more preferred embodiment, the raw materials for preparing the styrene-maleic amide acid copolymer further comprise, by weight, 30 to 80% of a solvent, 0.1 to 2% of an initiator, 0.5 to 5% of a molecular weight regulator, and styrene, alkylamine, and maleic anhydride, with the balance being made up.
In a more preferred embodiment, the raw materials for preparing the styrene-maleic amide acid copolymer further comprise 60% of a solvent, 1% of an initiator, 3% of a molecular weight regulator, styrene, an alkylamine and maleic anhydride, and the balance being made up by weight.
In a more preferred embodiment, the method for preparing the styrene maleamic acid copolymer comprises at least the following steps:
(1) preparation of maleamic acid: dissolving maleic anhydride in a solvent, and adding alkylamine for reaction;
(2) preparation of styrene maleamic acid copolymer: heating the solution reacted in the step (1), adding a mixed solution of an initiator, a molecular weight regulator and styrene, and reacting to obtain a polymer solution;
(3) and (3) purification treatment: and (3) cooling the polymer solution obtained in the step (2) to room temperature, adding an alcohol substance to precipitate a solid, and drying to obtain the polymer.
In a more preferred embodiment, the method for preparing the styrene maleamic acid copolymer comprises at least the following steps:
(1) preparation of maleamic acid: dissolving maleic anhydride in a solvent, stirring and mixing uniformly, controlling the temperature of an ice-water bath to be below 10 ℃, slowly dripping alkylamine while stirring, and stirring and reacting for 2-5 hours after dripping;
(2) preparation of styrene maleamic acid copolymer: heating the solution reacted in the step (1) to 60-150 ℃, adding a mixed solution of an initiator, a molecular weight regulator and styrene while stirring, and reacting for 1-5 hours to obtain a polymer solution;
(3) and (3) purification treatment: and (3) cooling the polymer solution obtained in the step (2) to room temperature, precipitating the polymer solution by using alcohols, drying and drying to obtain the polymer.
<Alkylamine>
The alkylamine is selected from one or a combination of more of monoalkylamine, dialkylamine, alkyl diamine, alkyl triamine and alkyl polyamine.
In a preferred embodiment, the alkylamine has 1 to 8 carbon atoms.
In a more preferred embodiment, the alkylamine is a mono-alkylamine and/or a di-alkylamine.
In a more preferred embodiment, the monoalkylamine is an alkylamine having one alkyl group and 1 to 4 carbon atoms in the alkyl group; the dialkylamine is an alkylamine containing two alkyl groups and containing 1-4 carbon atoms in each alkyl group.
In a more preferred embodiment, the monoalkylamine is selected from any one of monomethylamine, monoethylamine, monopropylamine, monobutylamine; the dialkyl amine is selected from any one of dimethylamine, diethylamine, methylethylamine, dipropylamine, dibutylamine, methylbutylamine, methylpropylamine, ethylpropylamine, ethylbutylamine and propylbutylamine.
In a more preferred embodiment, the alkylamine is a monoalkylamine; more preferably, the monoalkylamine is monomethylamine.
In a more preferred embodiment, the molar ratio of styrene to alkylamine to maleic anhydride is (1 to 3): (0.5-2): 1; more preferably, the molar ratio of styrene, alkylamine and maleic anhydride is 1: 1: 1.
the applicant finds that maleic anhydride is firstly dissolved in a solvent to react with monoalkylamine, especially monomethylamine, and then react with styrene, and the molar ratio of the styrene to the alkylamine to the maleic anhydride is controlled to be (1-3): (0.5-2): the copolymer prepared at the moment has better water solubility, has obvious special main chain and branched chain structure space effect, can be well combined with the surface of copper-gold toner in the metal pigment, enables the toner to be well dispersed in a system, does not contain free amine or ammonia, does not react with metal, can greatly reduce the generation of corrosion and deterioration, and is particularly suitable to be used as a dispersing agent of water-soluble metal pigment.
<Solvent(s)>
The solvent is selected from one or a combination of a plurality of benzene solvents, ketone solvents and ester solvents.
In a preferred embodiment, the benzene-based solvent includes, but is not limited to: toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, 1,2, 4-trimethylbenzene, 1,3, 5-trimethylbenzene, propylbenzene, isopropylbenzene, diethylbenzene, butylbenzene, isobutylbenzene, p-methylisopropylbenzene; such ketone solvents include, but are not limited to: acetone, butanone, methyl acetone, 2-pentanone, 3-methyl-2-butanone, 2-hexanone, 3-hexanone, 2-methyl-3-pentanone, 3-dimethyl-2-butanone, 4-methyl-2-pentanone, 2-heptanone, 3-heptanone, 4-heptanone, 2, 4-dimethyl-3-pentanone, 2-octanone, 2, 6-dimethyl-4-heptanone, cyclopentanone, cyclohexanone, cycloheptanone; the ester solvents include, but are not limited to: ethyl acetate, butyl acetate, benzyl acetate, phenyl acetate, methyl propionate, ethyl propionate, propyl propionate, butyl propionate, methyl butyrate, ethyl butyrate, propyl butyrate, or butyl butyrate.
In a more preferred embodiment, the solvent is toluene.
<Initiator>
The initiator is organic peroxide or azo compound.
In a preferred embodiment, the organic peroxides include, but are not limited to: dibenzoyl peroxide, dicumyl peroxide, bis (2, 4-dichlorobenzoyl) peroxide, diterbutyl peroxide, lauroyl peroxide, tert-butyl peroxybenzoate, diisopropyl peroxydicarbonate, or dicyclohexyl peroxydicarbonate; the azo compound initiators include, but are not limited to: azobisisobutyronitrile or azobisisoheptylcyanide.
In a more preferred embodiment, the initiator is azobisisobutyronitrile.
<Molecular weight regulator>
The molecular weight regulator is alkyl mercaptan and/or aromatic compound.
Examples of alkyl thiols include, but are not limited to: n-butyl mercaptan, n-octyl mercaptan, n-dodecyl mercaptan, t-dodecyl mercaptan, isopropyl mercaptan and n-pentyl mercaptan;
examples of aromatic compounds include, but are not limited to: alpha methyl styrene dimer, alpha ethyl styrene dimer and halogen compounds.
In a preferred embodiment, the molecular weight regulator is an α -methylstyrene dimer.
<AlcoholsSubstance(s)>
The alcohol substance is methanol or ethanol.
In a preferred embodiment, the alcohol is ethanol.
The second aspect of the present invention provides a styrene maleamic acid copolymer prepared according to the preparation method.
Examples
In order to better understand the above technical solutions, the following detailed descriptions will be provided with reference to specific embodiments. It should be noted that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and that the insubstantial modifications and adaptations of the present invention by those skilled in the art based on the above disclosure are still within the scope of the present invention. In addition, the starting materials used are all commercially available, unless otherwise specified.
Example 1
Embodiment 1 of the present invention provides a styrene maleamic acid copolymer, the preparation method of which comprises the steps of:
(1) preparation of maleamic acid: dissolving maleic anhydride in a solvent, stirring and mixing uniformly, controlling the temperature of an ice-water bath at 0 ℃, slowly dropwise adding alkylamine while stirring, and stirring and reacting for 3 hours after dropwise adding;
(2) preparation of styrene maleamic acid copolymer: heating the solution reacted in the step (1) to 110 ℃, adding a mixed solution of an initiator, a molecular weight regulator and styrene while stirring, and reacting for 3 hours to obtain a polymer solution;
(2) and (3) purification treatment: and (3) cooling the polymer solution obtained in the step (2) to room temperature, precipitating the polymer solution by using alcohols, drying and drying to obtain the polymer.
The alkylamine is monomethylamine; the molar ratio of the styrene to the alkylamine to the maleic anhydride is 1: 1: 1; the weight percentage of the solvent is 60%, the initiator is 1%, the molecular weight regulator is 3%, and the balance of styrene, alkylamine and maleic anhydride is complemented.
The solvent is toluene; the initiator is azodiisobutyronitrile; the molecular weight regulator is alpha-methyl styrene dimer; the alcohol substance is ethanol.
Example 2
Example 2 of the present invention provides a styrene maleamic acid copolymer, which is prepared in the same manner as in example 1.
The alkylamine is monomethylamine; the molar ratio of the styrene to the alkylamine to the maleic anhydride is 1: 0.5: 1; the weight percentage of the solvent is 60%, the initiator is 1%, the molecular weight regulator is 2%, and the balance of styrene, alkylamine and maleic anhydride is complemented.
The solvent is toluene; the initiator is azodiisobutyronitrile; the molecular weight regulator is alpha-methyl styrene dimer; the alcohol substance is ethanol.
Example 3
Example 3 of the present invention provides a styrene maleamic acid copolymer, which is prepared by the same method as in example 1.
The alkylamine is monomethylamine; the molar ratio of the styrene to the alkylamine to the maleic anhydride is 3: 2: 1; according to the weight percentage, the dosage of the solvent is 65 percent, the dosage of the initiator is 2 percent, the dosage of the molecular weight regulator is 4 percent, and the balance is made up by styrene, alkylamine and maleic anhydride.
The solvent is toluene; the initiator is azodiisobutyronitrile; the molecular weight regulator is alpha-methyl styrene dimer; the alcohol substance is ethanol.
Example 4
Example 4 of the present invention provides a styrene maleamic acid copolymer, which is the same as example 1 except that the molar ratio of styrene, alkylamine, and maleic anhydride is 1: 3: 1.
example 5
Example 5 of the present invention provides a styrene maleamic acid copolymer, which is the same as example 1 except that the molar ratio of styrene, alkylamine, and maleic anhydride is 1: 1: 3.
example 6
Example 6 of the present invention provides a styrene maleamic acid copolymer, which is the same as example 1, except that the alkylamine is diethylamine.
Example 7
Example 7 of the present invention provides a styrene maleamic acid copolymer, which is the same as example 1, except that the alkylamine is hexylamine.
Performance testing
The copolymer prepared in the embodiment 1-7 is added into deionized water and stirred uniformly to obtain a dispersing agent with a solid content of 30%, and 40 parts by weight of copper-gold powder, 17 parts of dispersing agent, 2 parts of sodium dodecyl sulfate, 1 part of BYK-028 defoaming agent (purchased from Bick chemical company) and 40 parts of deionized water are mixed uniformly to obtain the copper-gold color paste. A comparative example in which the dispersant was styrene acrylate ammonium salt was further set, and performance evaluation was performed on each of the materials.
1. Stability of
And (3) placing the prepared copper-gold color paste at room temperature for 1 month, observing whether the copper-gold color paste has the phenomena of skinning and sedimentation, respectively setting 100 parallel samples in each embodiment, and recording the skinning and sedimentation probabilities, namely the percentage of the number of the skinning and sedimentation copper-gold color pastes in the total test quantity.
2. Retention of metallic primary color
And (3) placing the prepared copper-gold color paste at room temperature, observing and recording the time of losing the primary color of the metal, respectively setting 100 parallel samples in each embodiment, and finally taking an average value.
TABLE 1
| Stability (%) | Time of losing metal primary color (d) | |
| Example 1 | 0 | >30 |
| Example 2 | 0 | >30 |
| Example 3 | 0 | >30 |
| Example 4 | 20 | <10 |
| Example 5 | 20 | <15 |
| Example 6 | 50 | <25 |
| Example 7 | 70 | <25 |
| Comparative example | 40 | <7 |
The foregoing examples are merely illustrative and serve to explain some of the features of the method of the present invention. The appended claims are intended to claim as broad a scope as is contemplated, and the examples presented herein are merely illustrative of selected implementations in accordance with all possible combinations of examples. Accordingly, it is applicants' intention that the appended claims are not to be limited by the choice of examples illustrating features of the invention. Also, where numerical ranges are used in the claims, subranges therein are included, and variations in these ranges are also to be construed as possible being covered by the appended claims.
Claims (6)
1. A preparation method of a styrene maleic amide acid copolymer is characterized by at least comprising the following steps:
(1) preparing maleamic acid;
(2) preparing a styrene maleic amide acid copolymer;
(3) purifying;
the raw materials for preparing the styrene-maleic amide acid copolymer comprise styrene, alkylamine and maleic anhydride; the molar ratio of the styrene to the alkylamine to the maleic anhydride is (1-3): (0.5-2): 1; the alkylamine is monoalkylamine; the monoalkylamine is monomethylamine.
2. The method for preparing styrene maleic amide acid copolymer according to claim 1, wherein the raw materials for preparing styrene maleic amide acid copolymer further comprise 30-80% by weight of solvent, 0.1-2% by weight of initiator, 0.5-5% by weight of molecular weight regulator, styrene, alkylamine and maleic anhydride to make up the balance.
3. The method for preparing styrene maleic amide acid copolymer according to claim 2, wherein the solvent is selected from one or more of benzene solvent, ketone solvent and ester solvent.
4. The method for preparing styrene maleic amide acid copolymer according to claim 2, wherein the initiator is organic peroxide or azo compound.
5. The method for preparing styrene maleic amide acid copolymer according to claim 2, wherein the molecular weight regulator is alkyl mercaptan and/or aromatic compound.
6. A styrene maleamic acid copolymer obtained by the production method according to any one of claims 1 to 5.
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| US8039550B2 (en) * | 2005-05-20 | 2011-10-18 | Akzo Nobel N.V. | Process for preparing a polymer dispersion and a polymer dispersion |
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| WO2017155694A1 (en) * | 2016-03-08 | 2017-09-14 | Huntsman Petrochemical Llc | Concentrated low viscosity agricultural formulations |
| CN107082887A (en) * | 2017-04-13 | 2017-08-22 | 佛山市贝特尔化工有限公司 | A kind of preparation method and applications of hyper-dispersant |
| CN109776710A (en) * | 2018-12-27 | 2019-05-21 | 苏州世名科技股份有限公司 | Structure containing phenylethylene-maleic anhydride and the waterborne pigment dispersant and preparation method thereof of graft modification |
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Address after: No. 448, outer ring road, Jiaxing Port District, Jiaxing, Zhejiang Applicant after: Jiaxing Huawen Chemical Co., Ltd Address before: 314000 No. 448, Waihuan West Road, port area, Jiaxing City, Zhejiang Province Applicant before: JIAXING HUAWEN CHEMICAL Co.,Ltd. |
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