CN114989428A - Preparation method of water-based resin and resin - Google Patents
Preparation method of water-based resin and resin Download PDFInfo
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- CN114989428A CN114989428A CN202210511166.4A CN202210511166A CN114989428A CN 114989428 A CN114989428 A CN 114989428A CN 202210511166 A CN202210511166 A CN 202210511166A CN 114989428 A CN114989428 A CN 114989428A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
Abstract
The invention discloses a preparation method of water-based resin and the resin, and the preparation method comprises the following steps: adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent to prepare a matrix sample; adding methylbenzene azeotropic distillation into a substrate sample, performing imine reaction after azeotropic distillation, adding 0.35-0.70 part by mass of epoxy group-containing acrylate, a polymerization inhibitor and a catalyst, and adding triethylamine to prepare a crude solution; and washing the crude solution, and then carrying out suction filtration to obtain the water-based resin. According to the preparation method, an acyl chlorination process is not needed, the principle that an epoxy group can react with-COOH mildly is utilized on the side chain of the polyamic acid, a compound with an unsaturated bond and the epoxy group is selected, and an unsaturated double bond group is directly introduced to the side chain of the polyamic acid, so that the polyimide is obtained, and the adverse effect of chloride ions in a polyimide product on an optoelectronic device due to acyl chlorination is avoided.
Description
Technical Field
The invention belongs to the technical field of polyimide resin materials, and particularly relates to a preparation method of a water-based resin and the resin.
Background
Polyimide is a rigid chain polymer with a chemical structure and a highly regular structure, the main chain of which contains imide rings, is a high polymer material with excellent comprehensive performance, has incomparable excellent high and low temperature resistance and mechanical performance of other high polymers, can resist the temperature of more than 400 ℃, has the temperature range of minus 200 ℃ plus 300 ℃ for long-time use, has outstanding high and low temperature resistance as an electronic information material, has outstanding dielectric performance and radiation resistance, is one of the best packaging and coating materials in the field of current microelectronic information, and is widely applied to the fields of aviation, aerospace, traffic, ship manufacturing, electromechanics, microelectronics, liquid crystal display, chemical industry and the like. In addition, polyimide resin shows comprehensive excellent performance in the aspects of adhesives, fibers, flexible circuit boards, photoresist and the like, and the polyimide has a great application prospect which is fully recognized whether being used as a structural material or a functional material.
In the polyimide process containing unsaturated double bonds, the process of acyl chlorination cannot be avoided, the prepared product is directly polycondensed with alcohol or diamine of unsaturated double bonds without separation, chloride ions generated in the reaction are difficult to remove, the method has adverse effects on optical devices, and the process is long.
Disclosure of Invention
Objects of the invention
The invention aims to provide a preparation method of a water-based resin and the resin, so as to solve the technical problem that chloride ions of a polyimide resin material produced in the prior art are difficult to remove.
(II) technical scheme
In order to solve the above problems, a first aspect of the present invention provides a method for preparing an aqueous resin, comprising: adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent to prepare a matrix sample; the mass part of the solvent is 1-4 times of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride; adding methylbenzene azeotropic distillation into the matrix sample, and performing imine reaction after the azeotropic distillation to obtain a polyimide solution; adding 0.35-0.70 part by mass of acrylic ester with epoxy groups into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution; adding triethylamine into the viscous transparent yellow glue solution until the pH value is 4.5-5 to prepare a crude solution; and washing the crude solution, and then carrying out suction filtration to obtain the water-based resin.
Further, the solvent is one of dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide.
Further, the step of adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into the solvent to prepare the matrix sample comprises the following steps: adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent, and stirring at the temperature of 0-20 ℃ for 2.5-3.5h to obtain the matrix sample.
Further, the conditions of the azeotropic distillation are as follows: introducing nitrogen for protection and heating; the heating temperature is 110-120 ℃.
Further, the imine reaction comprises: carrying out imine reaction at 115-125 ℃ for 2-4h, and then reducing the temperature to 90-100 ℃.
Further, the step of adding 0.35-0.70 parts by mass of acrylic ester with epoxy groups into the polyimide solution to obtain a viscous transparent yellow glue solution after reaction comprises the following steps: adding 0.35-0.70 parts by weight of acrylic ester with epoxy group, polymerization inhibitor and catalyst into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution; the catalyst is triphenylphosphine, and the mass part of the triphenylphosphine is 5-7 per mill of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride; the polymerization inhibitor is p-hydroxyanisole, and the mass part of the polymerization inhibitor is 0.1-0.15 per thousand of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride.
Further, the step of obtaining the viscous transparent yellow glue solution after the reaction comprises: reacting at the temperature of 100 ℃ and 120 ℃ for 1.5-3h, and cooling to room temperature to obtain viscous transparent yellow glue solution.
Further, the step of washing and filtering the crude solution to obtain the water-based resin comprises the following steps: stirring the crude solution for 20-40min, washing with an ethanol solution for multiple times, performing suction filtration, and drying a solid product subjected to suction filtration under a vacuum condition to constant weight; the vacuum degree under the vacuum condition is 0.08-0.09 MPa; the drying temperature is 75-85 ℃.
Further, the aromatic dicarboxylic anhydride is: one or more of pyromellitic dianhydride, perylene tetracarboxylic dianhydride, tetrahydrophthalic anhydride, 4 '-diphenyl ether tetracarboxylic dianhydride, 4' -diphenyl ether tetracarboxylic dianhydride and naphthalene tetracarboxylic dianhydride;
further, the acrylic ester with epoxy group is: one or more of glycidyl methacrylate, glycidyl acrylate and allyl glycidyl ether;
further, the aromatic diamine is: 4,4 '-diaminodiphenyl ether, p-phenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, diaminodiphenyl sulfide, 2' -diaminodiphenyldisulfide, 3 '-dimethyl-4, 4' -diaminodiphenylmethane.
According to another aspect of the present invention, there is provided a water-based polyimide acrylic resin prepared by the preparation method according to any one of the above technical schemes.
(III) advantageous effects
The technical scheme of the invention has the following beneficial technical effects:
according to the preparation method, an acyl chlorination process is not needed, the principle that an epoxy group can react with-COOH mildly is utilized on the side chain of the polyamide acid (PAA), a compound with an unsaturated bond and an epoxy group is selected, and an unsaturated double bond group is directly introduced to the side chain of the polyamide acid (PAA), so that the polyimide is obtained, and the adverse effect of chloride ions in a polyimide product on an optoelectronic device due to acyl chlorination is avoided. The water-based resin prepared by the preparation method has certain hydrophilicity and water absorption, and also has the advantages of no solvent odor, no toxicity, no pollution, convenient operation, easy cleaning of residual glue, high solid content, safe and convenient storage and transportation, and the like. The aqueous resin prepared by the preparation method belongs to polyimide acid with low polymerization degree, the amount of unsaturated double bonds of the aqueous resin increases with the decrease of the polymerization degree, and the water solubility of the aqueous resin increases with the decrease of the polymerization degree.
Drawings
FIG. 1 is a flow chart of a method for preparing an aqueous resin according to an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in further detail with reference to the accompanying drawings in conjunction with the following detailed description. It is to be understood that these descriptions are only illustrative and are not intended to limit the scope of the present invention. Moreover, in the following description, descriptions of well-known structures and techniques are omitted so as to not unnecessarily obscure the concepts of the present invention.
In the drawings a schematic view of a layer structure according to an embodiment of the invention is shown. The figures are not drawn to scale, wherein certain details are exaggerated and possibly omitted for clarity. The shapes of various regions, layers, and relative sizes and positional relationships therebetween shown in the drawings are merely exemplary, and deviations may occur in practice due to manufacturing tolerances or technical limitations, and a person skilled in the art may additionally design regions/layers having different shapes, sizes, relative positions, as actually required.
It is to be understood that the embodiments described are only a few embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Furthermore, the technical features involved in the different embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
The invention will be described in more detail below with reference to the accompanying drawings. Like elements in the various figures are denoted by like reference numerals. For purposes of clarity, the various features in the drawings are not necessarily drawn to scale.
ODA, called Octadecylamine, CH 3 (CH 2 ) 16 CH 2 NH 2 Abbreviation of (d), chinese name: 4,4' -diaminodiphenyl ether.
PMDA, known collectively as Benzenetetracarboxylic anhydride, C 10 H 2O6 Abbreviation of (d), chinese name: pyromellitic dianhydride.
NMP, known as N-Methylpyrrolidone, C 5 H 9 Abbreviation of NO, chinese name: n-methyl pyrrolidone.
In an embodiment of the present invention, there is provided a method for preparing an aqueous resin, which may include: adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent to prepare a matrix sample; the mass part of the solvent is 1-4 times of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride; adding methylbenzene azeotropic distillation into the matrix sample, and performing imine reaction after the azeotropic distillation to obtain a polyimide solution; adding 0.35-0.70 parts by weight of acrylic ester with epoxy groups into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution; adding triethylamine into the viscous transparent yellow glue solution until the pH value is 4.5-5 to prepare a crude solution; and washing the crude solution, and then carrying out suction filtration to obtain the water-based resin.
According to the preparation method, an acyl chlorination process is not needed, a principle that an epoxy group can react with-COOH mildly is utilized on a side chain of polyamide acid (PAA), a compound with an unsaturated bond and an epoxy group is selected, and the unsaturated double bond group is directly introduced to the side chain of the polyamide acid (PAA), so that polyimide is obtained, and adverse effects of chloride ions in a polyimide product on an optoelectronic device due to acyl chlorination are avoided. The water-based resin prepared by the preparation method has certain hydrophilicity and water absorption, and also has the advantages of no solvent odor, no toxicity, no pollution, convenient operation, easy cleaning of residual glue, high solid content, safe and convenient storage and transportation, and the like. The aqueous resin prepared by the preparation method belongs to polyimide acid with low polymerization degree, the amount of unsaturated double bonds of the aqueous resin increases with the decrease of the polymerization degree, and the water solubility of the aqueous resin increases with the decrease of the polymerization degree.
And adding toluene into the matrix sample, wherein the toluene and water can form an azeotropic system, and water is discharged out of the reaction system through azeotropy to ensure that the reaction is carried out, and the toluene cannot react with other substances in the solution. The addition of toluene can facilitate the imine reaction. And water generated by the reaction can be removed.
In an alternative embodiment, the washing of the crude solution is performed with one or more of ethanol, or methanol, or isopropanol.
And after the crude solution is washed, a liquid polymer is separated out in ethanol or methanol or isopropanol so as to realize liquid-liquid separation, and the solution is subjected to suction filtration after precipitation.
In a preferred embodiment, the washing of the crude solution is performed with ethanol.
In an alternative embodiment, the solvent is one of dimethylformamide, N-methylpyrrolidone, and dimethylsulfoxide.
In an alternative embodiment, the solvent is N-methylpyrrolidone.
In an alternative embodiment, the adding 1 part by mass of aromatic diamine and 1.36 to 3 parts by mass of aromatic dicarboxylic anhydride to the solvent to prepare the matrix sample may include: adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent, and stirring at the temperature of 0-20 ℃ for 2.5-3.5h to obtain the matrix sample.
In an alternative embodiment, the conditions of the azeotropic distillation are: introducing nitrogen for protection and heating.
In an alternative embodiment, the heating temperature of the azeotropic distillation is 110-120 ℃.
In an alternative embodiment, the imine reaction may include: carrying out imine reaction at 115-125 ℃ for 2-4h, and then reducing the temperature to 90-100 ℃.
In an optional embodiment, the step of adding 0.35 to 0.70 parts by mass of acrylate with epoxy group to the polyimide solution to obtain a viscous transparent yellow glue solution after reaction comprises: and adding 0.35-0.70 part by mass of acrylic ester with epoxy group, a polymerization inhibitor and a catalyst into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution.
In an alternative embodiment, the catalyst is triphenylphosphine, and the mass part of the triphenylphosphine is 5-7 per mill of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride.
In an optional embodiment, the polymerization inhibitor is p-hydroxyanisole, and the mass part of the polymerization inhibitor is 0.1-0.15 per mill of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride.
In an alternative embodiment, the obtaining of the viscous transparent yellow glue solution after the reaction may include: reacting at the temperature of 100 ℃ and 120 ℃ for 1.5-3h, and cooling to room temperature to obtain viscous transparent yellow glue solution.
In an alternative embodiment, the washing and suction-filtering the crude solution to obtain the aqueous resin may comprise: and (3) stirring the crude solution for 20-40min, washing the crude solution for multiple times by using an ethanol solution, carrying out suction filtration, and drying a solid product subjected to suction filtration under a vacuum condition to constant weight.
In an alternative embodiment, the vacuum degree of the vacuum condition is 0.08-0.09 MPa.
In an alternative embodiment, the temperature of the drying is 75-85 ℃.
In an alternative embodiment, the aromatic dicarboxylic anhydride is: one or more of pyromellitic dianhydride, perylene tetracarboxylic dianhydride, tetrahydrophthalic anhydride, 4 '-diphenyl ether tetracarboxylic dianhydride, 4' -diphenyl ether tetracarboxylic dianhydride and naphthalene tetracarboxylic dianhydride.
In an alternative embodiment, the acrylate with an epoxy group is: one or more of glycidyl methacrylate, glycidyl acrylate and allyl glycidyl ether;
in an alternative embodiment, the aromatic diamine is: 4,4 '-diaminodiphenyl ether, p-phenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, diaminodiphenyl sulfide, 2' -diaminodiphenyldisulfide, 3 '-dimethyl-4, 4' -diaminodiphenylmethane.
Fig. 1 is a flow chart of a method for preparing an aqueous resin according to an embodiment of the present invention.
In an embodiment of the present invention, a method for preparing an aqueous resin is provided, which at least includes the following steps:
s100, adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent to prepare a matrix sample.
S200, adding methylbenzene to the matrix sample, and performing azeotropic distillation, and performing imine reaction after the azeotropic distillation to obtain a polyimide solution.
Aromatic diamine and aromatic dicarboxylic anhydride are adopted to prepare polyimide resin with low polymerization degree and carboxyl, acrylic ester with epoxy group is selected to react with partial-COOH in the polyimide resin, and the residual-COOH is neutralized by organic amine to obtain aqueous polyimide acrylic resin solution.
S300, adding 0.35-0.70 parts by weight of acrylic ester with epoxy groups into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution.
S400, adding triethylamine into the viscous transparent yellow glue solution until the pH value is 4.5-5 to obtain a crude solution.
S500, washing the crude solution, and performing suction filtration to obtain the water-based resin.
According to the preparation method, an acyl chlorination process is not needed, the principle that an epoxy group can react with-COOH mildly is utilized on the side chain of the polyamide acid (PAA), a compound with an unsaturated bond and an epoxy group is selected, and an unsaturated double bond group is directly introduced to the side chain of the polyamide acid (PAA), so that the polyimide is obtained, and the adverse effect of chloride ions in a polyimide product on an optoelectronic device due to acyl chlorination is avoided. The water-based resin prepared by the preparation method has certain hydrophilicity and water absorption, and also has the advantages of no solvent odor, no toxicity, no pollution, convenient operation, easy cleaning of residual glue, high solid content, safe and convenient storage and transportation, and the like. The aqueous resin prepared by the preparation method belongs to polyimide acid with low polymerization degree, the amount of unsaturated double bonds of the aqueous resin increases with the decrease of the polymerization degree, and the water solubility of the aqueous resin increases with the decrease of the polymerization degree.
Example 1:
1 part of ODA (molecular weight 200), 1.36 to 3 parts of PMDA (molecular weight 218), and 1 to 4 parts of NMP (N-methylpyrrolidone, boiling point: 203 ℃) as a solvent based on the total amount of ODA and PMDA were charged into a four-necked flask equipped with a condenser tube and reacted at 0 to 20 ℃ for 3 hours with stirring. Adding 1-3 parts of toluene (boiling point 110.6 ℃), introducing nitrogen for protection, heating, carrying out imidization reaction at 120 ℃ for 2-4h after the azeotrope of toluene and water is distilled, and then cooling to 90-100 ℃ for standby application to complete the synthesis of the carboxyl-terminated polyimide resin (i.e. the polyimide solution).
0.35-0.70 part of glycidyl methacrylate (M ═ 142), 0.1-0.15 per thousand of total amount of ODA and PMDA (polymerization inhibitor), 5-7 per thousand of total amount of ODA and PMDA (triphenylphosphine) (catalyst) are added into the polyimide solution, and the reaction is carried out for 1.5-3h at the temperature of 100-120 ℃. Cooling to room temperature to obtain viscous transparent yellow glue solution.
Triethylamine (M101) is added into the viscous transparent yellow glue solution until the pH value is 8.0-9.0, the mixture is stirred for 30min, and then the glue solution is slowly injected into a filter flask to be repeatedly washed by ethanol solution and filtered. And finally, placing the suction filtration product in a vacuum drying oven, drying the product at 80 ℃ under the vacuum degree of 0.09MPa to constant weight to obtain the solid water-based polyimide acrylic resin (namely the water-based resin).
In an alternative embodiment, the mixed solvent of ethanol and NMP can be recycled.
In another embodiment of the present invention, a water-based polyimide acrylic resin is provided, which is prepared by the preparation method according to any one of the above technical schemes.
The water-based resin prepared by the preparation method has certain hydrophilicity and water absorption, and also has the advantages of no solvent odor, no toxicity, no pollution, convenient operation, easy cleaning of residual glue, high solid content, safe and convenient storage and transportation, and the like. The aqueous resin prepared by the preparation method belongs to polyimide acid with low polymerization degree, the amount of unsaturated double bonds of the aqueous resin increases with the decrease of the polymerization degree, and the water solubility of the aqueous resin increases with the decrease of the polymerization degree.
The invention aims to protect a preparation method of a water-based resin and the resin, and the preparation method of the water-based resin can comprise the following steps: adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent to prepare a matrix sample; the mass part of the solvent is 1-4 times of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride; adding methylbenzene azeotropic distillation into the matrix sample, and performing imine reaction after the azeotropic distillation to obtain a polyimide solution; adding 0.35-0.70 parts by weight of acrylic ester with epoxy group, polymerization inhibitor and catalyst into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution; adding triethylamine into the viscous transparent yellow glue solution until the pH value is 4.5-5 to prepare a crude solution; and washing the crude solution, and then carrying out suction filtration to obtain the water-based resin. According to the preparation method, an acyl chlorination process is not needed, the principle that an epoxy group can react with-COOH mildly is utilized on the side chain of the polyamide acid (PAA), a compound with an unsaturated bond and an epoxy group is selected, and an unsaturated double bond group is directly introduced to the side chain of the polyamide acid (PAA), so that the polyimide is obtained, and the adverse effect of chloride ions in a polyimide product on an optoelectronic device due to acyl chlorination is avoided. The water-based resin prepared by the preparation method has certain hydrophilicity and water absorption, and also has the advantages of no solvent odor, no toxicity, no pollution, convenient operation, easy cleaning of residual glue, high solid content, safe and convenient storage and transportation, and the like. The aqueous resin prepared by the preparation method belongs to polyimide acid with low polymerization degree, the amount of unsaturated double bonds of the aqueous resin increases with the decrease of the polymerization degree, and the water solubility of the aqueous resin increases with the decrease of the polymerization degree.
It is to be understood that the above-described embodiments of the present invention are merely illustrative of or explaining the principles of the invention and are not to be construed as limiting the invention. Therefore, any modification, equivalent replacement, improvement and the like made without departing from the spirit and scope of the present invention should be included in the protection scope of the present invention. Further, it is intended that the appended claims cover all such variations and modifications as fall within the scope and boundaries of the appended claims or the equivalents of such scope and boundaries.
Claims (10)
1. A method for preparing a water-based resin, comprising:
adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent to prepare a matrix sample; the mass part of the solvent is 1-4 times of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride;
adding methylbenzene azeotropic distillation into the matrix sample, and performing imine reaction after the azeotropic distillation to obtain a polyimide solution;
adding 0.35-0.70 parts by weight of acrylic ester with epoxy groups into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution;
adding triethylamine into the viscous transparent yellow glue solution until the pH value is 4.5-5 to prepare a crude solution;
and washing the crude solution, and then carrying out suction filtration to obtain the water-based resin.
2. The method for producing an aqueous resin according to claim 1,
the solvent is one of dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide.
3. The method for preparing the aqueous resin according to claim 1, wherein the step of adding 1 part by mass of the aromatic diamine and 1.36 to 3 parts by mass of the aromatic dicarboxylic anhydride to the solvent to prepare the matrix sample comprises:
adding 1 part by mass of aromatic diamine and 1.36-3 parts by mass of aromatic dicarboxylic anhydride into a solvent, and stirring at the temperature of 0-20 ℃ for 2.5-3.5h to obtain the matrix sample.
4. The method for producing an aqueous resin according to claim 1,
the conditions of the azeotropic distillation are as follows: introducing nitrogen for protection and heating;
the heating temperature is 110-120 ℃.
5. The method of claim 1, wherein the imine reaction comprises:
the temperature is reduced to 90-100 ℃ after imine reaction is carried out for 2-4h at the temperature of 115-125 ℃.
6. The preparation method of the aqueous resin according to claim 1, wherein the step of adding 0.35 to 0.70 parts by mass of the acrylate with the epoxy group into the polyimide solution to obtain a viscous transparent yellow glue solution after the reaction comprises:
adding 0.35-0.70 parts by weight of acrylic ester with epoxy group, polymerization inhibitor and catalyst into the polyimide solution, and reacting to obtain viscous transparent yellow glue solution;
the catalyst is triphenylphosphine, and the mass part of the triphenylphosphine is 5-7 permillage of the sum of the mass parts of the aromatic diamine and the aromatic dicarboxylic anhydride;
the polymerization inhibitor is p-hydroxyanisole, and the mass part of the polymerization inhibitor is 0.1-0.15 per thousand of the total mass part of the aromatic diamine and the aromatic dicarboxylic anhydride.
7. The method for preparing the water-based resin according to claim 1, wherein the step of obtaining the viscous transparent yellow glue solution after the reaction comprises the following steps:
reacting at the temperature of 100 ℃ and 120 ℃ for 1.5-3h, and cooling to room temperature to obtain viscous transparent yellow glue solution.
8. The method for preparing the water-based resin according to claim 1, wherein the washing and suction-filtering the crude solution to obtain the water-based resin comprises:
stirring the crude solution for 20-40min, washing with an ethanol solution for multiple times, performing suction filtration, and drying a solid product subjected to suction filtration under a vacuum condition to constant weight;
the vacuum degree under the vacuum condition is 0.08-0.09 MPa;
the drying temperature is 75-85 ℃.
9. The method for producing an aqueous resin according to any one of claims 1 to 8,
the aromatic dicarboxylic anhydride is: one or more of pyromellitic dianhydride, perylene tetracarboxylic dianhydride, tetrahydrophthalic anhydride, 4 '-diphenyl ether tetracarboxylic dianhydride, 4' -diphenyl ether tetracarboxylic dianhydride and naphthalene tetracarboxylic dianhydride;
the acrylic ester with epoxy group is as follows: one or more of glycidyl methacrylate, glycidyl acrylate and allyl glycidyl ether;
the aromatic diamine is: 4,4 '-diaminodiphenyl ether, p-phenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, diaminodiphenyl sulfide, 2' -diaminodiphenyldisulfide, 3 '-dimethyl-4, 4' -diaminodiphenylmethane.
10. A water-based polyimide acrylic resin, which is produced by the production method according to any one of claims 1 to 9.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080146692A1 (en) * | 2004-12-16 | 2008-06-19 | Ryuji Uehara | Unsaturated Group-Containing Polyimide Resin, Photosensitive Resin Composition Containing Same, And Cured Product Thereof |
| CN103122231A (en) * | 2013-03-11 | 2013-05-29 | 东华大学 | 1,4-di(2,4-diamino phenoxy) benzenoid form high-temperature epoxy adhesive and preparation method thereof |
| CN105153127A (en) * | 2015-10-13 | 2015-12-16 | 中国科学院兰州化学物理研究所 | Polyimide oligomer capable of quick photocuring and preparation method and application thereof |
| CN113308153A (en) * | 2021-05-17 | 2021-08-27 | 江国长 | Heat-resistant easy-to-clean coating and preparation method thereof |
-
2022
- 2022-05-11 CN CN202210511166.4A patent/CN114989428A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080146692A1 (en) * | 2004-12-16 | 2008-06-19 | Ryuji Uehara | Unsaturated Group-Containing Polyimide Resin, Photosensitive Resin Composition Containing Same, And Cured Product Thereof |
| CN103122231A (en) * | 2013-03-11 | 2013-05-29 | 东华大学 | 1,4-di(2,4-diamino phenoxy) benzenoid form high-temperature epoxy adhesive and preparation method thereof |
| CN105153127A (en) * | 2015-10-13 | 2015-12-16 | 中国科学院兰州化学物理研究所 | Polyimide oligomer capable of quick photocuring and preparation method and application thereof |
| CN113308153A (en) * | 2021-05-17 | 2021-08-27 | 江国长 | Heat-resistant easy-to-clean coating and preparation method thereof |
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