CN111574923A - Polyamide-imide insulating paint and preparation method thereof - Google Patents
Polyamide-imide insulating paint and preparation method thereof Download PDFInfo
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- CN111574923A CN111574923A CN202010468921.6A CN202010468921A CN111574923A CN 111574923 A CN111574923 A CN 111574923A CN 202010468921 A CN202010468921 A CN 202010468921A CN 111574923 A CN111574923 A CN 111574923A
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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
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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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
- C08G73/14—Polyamide-imides
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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Abstract
The invention relates to a polyamide-imide insulating paint and a preparation method thereof, wherein the preparation method comprises the following steps: dissolving MDA and TMA in an amide organic solvent, heating to 125-130 ℃ at the speed of 15-20 ℃/h for reaction, and cooling to below 50 ℃ after the reaction is completed to obtain a DIDC intermediate; wherein the molar ratio of 4,4' -diphenylmethane diamine to trimellitic anhydride is 0.45-0.5: 1; reacting the product with MDI in an ester solvent under the action of a phase transfer catalyst, heating to 95-100 ℃ at the heating rate of 15-20 ℃/h for constant temperature reaction for 2-3h, then heating to 115-120 ℃ at the heating rate of 15-20 ℃/h for reaction, adding an amide organic solvent and an end-capping agent when the acid value of a reaction solution is 6.4-7.2, then cooling to 60-70 ℃, and adding the amide organic solvent and an aromatic hydrocarbon diluent to obtain the polyamide-imide insulating coating.
Description
Technical Field
The invention relates to the field of insulating coatings, in particular to a polyamide-imide insulating coating and a preparation method thereof.
Background
The polyamide-imide insulating paint has excellent mechanical and electric performance and heat resistance grade of 220. The main chain structure of the polyamide-imide contains amido bonds and imide rings, and the polymer has the advantages of both polyamide and polyimide. The performance of the material is between the two, and the general structure is as follows:
wherein the content of the first and second substances,
the main chain of the polymer contains amido-NH-CO-, so that the rigidity of the chain is reduced, the solubility is improved, the polymer is easy to process and has better viscosity, and the wear resistance and alkali resistance of the product are improved, so that the polymer is widely applied to occasions with poorer working conditions, such as compressors, wind power generation, large-scale electric tools and the like.
The method for synthesizing polyamide-imide has many methods, and the prior methods for synthesizing polyamide-imide comprise an acyl chloride method, a polycondensation method, a diisocyanate method and the like, and the advantages and the disadvantages of the several methods are analyzed as follows:
1. the method for preparing polyamide-imide by using trimellitic anhydride and thionyl chloride is characterized in that trimellitic anhydride acyl chloride is prepared by using trimellitic anhydride and thionyl chloride under the action of concentrated sulfuric acid and pyridine, then the trimellitic anhydride acyl chloride reacts with diamine to generate polyamide acid, and finally the polyamide acid is cyclized to obtain polyamide-imide.
2. The polycondensation method is prepared by directly polycondensing trimellitic anhydride and diamine, and has the advantages of cheap raw materials and simple process, but the amino group has low activity, can easily react with an anhydride group, is difficult to react with a carboxylic acid group, and generally can react at high temperature or by adding a catalyst.
3. The diisocyanate method is prepared by directly condensing diisocyanate and trimellitic anhydride as raw materials to remove carbon dioxide, has low requirements on process and equipment, is simple to operate, is the mainstream production method at present, and has the defects of high toxicity, difficult transportation and storage, high price and the like of the raw material isocyanate.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a polyamide-imide insulating paint and a preparation method thereof.
The first purpose of the invention is to disclose a preparation method of polyamide-imide insulating paint, which comprises the following steps:
(1) dissolving 4,4' -diphenylmethane diamine (MDA) and trimellitic anhydride (TMA) in an amide organic solvent, heating to 125-130 ℃ at the speed of 15-20 ℃/h for reaction, and cooling to below 50 ℃ after the reaction is completed to obtain a DIDC intermediate; wherein the molar ratio of 4,4' -diphenylmethane diamine to trimellitic anhydride is 0.45-0.5: 1;
(2) reacting the product obtained in the step (1) with diphenylmethane diisocyanate (MDI) in an ester solvent under the action of a phase transfer catalyst, wherein the molar number of the diphenylmethane diisocyanate is the same as that of the 4,4' -diphenylmethane diamine in the step (1), the phase transfer catalyst is a quaternary ammonium salt or quaternary phosphonium salt phase transfer catalyst, and the reaction comprises
Heating to 95-100 ℃ at the heating rate of 15-20 ℃/h for constant temperature reaction for 2-3h, heating to 115-120 ℃ at the heating rate of 15-20 ℃/h for reaction, and adding an amide organic solvent and a blocking agent to block unreacted isocyanate groups when the acid value of the reaction solution is 6.4-7.2;
(3) and (3) cooling the reaction liquid obtained in the step (2) to 60-70 ℃, and adding an amide organic solvent and an aromatic hydrocarbon diluent to obtain the polyamide-imide insulating coating.
Further, in the step (1), the amide-based organic solvent is selected from one or more of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide and N, N-diethylformamide. Wherein, the N-methyl pyrrolidone belongs to lactam organic solvents.
Further, the ratio of trimellitic anhydride to the amide-based organic solvent is 1 mol: 400 and 600 ml.
Further, in the step (1), in the reaction process, azeotropic dehydration is carried out until the dehydration amount reaches more than the theoretical amount of 85%, an infrared spectrogram of the reaction solution is detected, and the reaction is completed when the amine group on the infrared spectrogram is completely disappeared.
Further, in the step (1), after the reaction is completed, the structural formula of the obtained DIDC intermediate is as follows:
the DIDC intermediate prepared above is a monomer having two carboxylic acid groups because trimellitic anhydride and 4,4' -diphenylmethane diamine have a molar ratio of 2:1 in step (1) and amine groups preferentially react with anhydride groups.
Further, in the step (2), the phase transfer catalyst is one or more of quaternary ammonium salt type phase transfer catalyst, quaternary phosphonium salt type phase transfer catalyst and polyethylene glycol with the weight average molecular weight of 200-6000/mol.
Further, in the step (2), the quaternary ammonium salt catalyst includes tetramethylammonium bromide, tetrabutylammonium bromide, benzyltrimethylammonium chloride, trioctylmethylammonium chloride, hexadecyltrimethylammonium bromide, and the like.
Further, in the step (2), the quaternary phosphonium salt type phase transfer catalyst includes triphenylethylphosphonium bromide, tetraphenylphosphonium chloride, benzyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, tetrakis (diethylamino) phosphonium bromide, triphenylbutylphosphonium bromide, triphenylethylphosphonium bromide and the like.
Further, in the step (2), the ester solvent includes, but is not limited to, dimethyl succinate, dimethyl glutarate, dimethyl adipate, diethyl succinate, diethyl adipate, γ -butyrolactone, propylene carbonate, etc.; the ratio of the ester solvent to the product of step (1) was 150-300 ml: 1 mol.
Further, in the step (2), when the acid value of the reaction solution is 6.4 to 7.2, the structural formula of the obtained product is as follows:
the molecular weight of the product was 15000-25000 g/mol.
Further, in the step (2), the alcohol-based capping agent is selected from one or a combination of methanol, ethanol, tert-butyl alcohol and benzyl alcohol.
Further, in step (3), the aromatic hydrocarbon diluent includes, but is not limited to, one or more of toluene, xylene, 100# white spirit, 150# white spirit, phenol and cresol.
Further, the polyamide imide insulating varnish has a solid content of 31 to 33% (200 ℃ C. times.2 h.times.1.5 g) and a viscosity of 7.50 to 12.5dPa.s (30 ℃ C.).
The method adopts two steps of reaction, wherein in the first step, diamine and trimellitic anhydride are adopted as raw materials to generate a DIDC intermediate; and in the second step, diisocyanate is reacted with the DIDC intermediate to produce the polyamideimide coating.
In the second step of reaction, the product obtained in the step (1) and MDI are reacted in an ester solvent, and the DIDC intermediate has poor solubility, so the ester solvent with strong dissolving power is selected. In addition, too much solvent that is soluble in the DIDC intermediate affects the solubility of the final resin, so an appropriate amount of solvent is beneficial to the appearance and workability of the coating.
In the second step of reaction, the product obtained in the step (1) and MDI react under the action of a phase transfer catalyst, and a DIDC intermediate has poor solubility and cannot participate in the reaction well, so that the reaction rate can be effectively increased by adding a quaternary ammonium salt or quaternary phosphonium salt phase transfer catalyst.
In the second step of reaction, the alcohol end-capping reagent is selected, so that the crosslinking of the polyamide-imide insulating coating during the film forming of the polyamide-imide wire enamel is facilitated.
The second purpose of the invention is to provide a polyamide-imide insulating paint prepared by the preparation method, wherein the polyamide-imide insulating paint comprises polyamide-imide, and the polyamide-imide comprises the following structural formula:
the molecular weight of the polyamideimide is 15000-25000 g/mol.
Further, the polyamideimide insulating coating prepared as described above has a solid content of 31 to 33% (200 ℃ C. times.2 h.times.1.5 g) and a viscosity of 7.50 to 12.5dPa.s (30 ℃ C.).
By the scheme, the invention at least has the following advantages:
in the synthetic process of the polyamide-imide insulating varnish, the advantages of a polycondensation method and a diisocyanate method are combined, the reaction is divided into two steps, in the first step, diamine is reacted with an anhydride group of trimellitic anhydride to form a DIDC intermediate; and in the second step, diisocyanate with higher activity is used for reacting with carboxylic acid groups of the DIDC intermediate, so that the use amount of the diisocyanate is reduced, and the finally prepared polyamide-imide insulating paint has good insulating property, good heat resistance and refrigerant resistance and reduced environmental pollution.
The foregoing is a summary of the present invention, and in order to provide a clear understanding of the technical means of the present invention and to be implemented in accordance with the present specification, the following is a preferred embodiment of the present invention and is described in detail below.
Drawings
FIG. 1 is a graph of the refrigerant test results of example 2 and comparative example coatings after they were formed into line samples and soaked in refrigerant.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
In the following examples of the present invention, the DBE solvent used was a combination of three solvents, dimethyl succinate, dimethyl glutarate and dimethyl adipate.
Example 1
(1) At normal temperature, adding 200ml of N-methyl pyrrolidone and 400ml of N, N-dimethylacetamide into a reaction container, then adding 198g of MDA and 384g of TMA, heating the obtained mixed solution to 130 ℃ at a heating rate of 15-20 ℃/h for constant-temperature reaction, carrying out azeotropic dehydration in the reaction process until the dehydration amount reaches over 85 wt% of the theoretical amount, sampling and detecting an infrared spectrogram of the reaction solution, and carrying out secondary distillation when the signal peak of amino groups (a stretching vibration peak 3400 and 3500 cm) on the infrared spectrogram-1) And when the intermediate DIDC completely disappears, cooling to below 50 ℃ to obtain an intermediate DIDC solution (the intermediate DIDC is not completely dissolved).
(2) Adding 250g of MDI, 150ml of DBE solvent, 50ml of gamma-butyrolactone and 6g of phase transfer catalyst tetrakis (diethylamino) phosphonium bromide (TPB) into the solution obtained in the step (1), heating to 100 ℃ at the heating rate of 15-20 ℃/h again, reacting for 3h at constant temperature, then heating to 120 ℃ at the heating rate of 20 ℃/h for constant-temperature reaction, observing that the reaction solution is changed from turbid to transparent when the reaction generates carbon dioxide and obviously reduces, starting to detect the acid value, when the acid value is 6.4-7.2, 300ml of N, N-dimethylformamide solvent and 60g of benzyl carbinol are added to block unreacted isocyanate groups, and then cooling to 70 ℃, adding 300ml of N, N-dimethylformamide, 200ml of xylene and 100ml of 100# petroleum solvent, and adjusting to a proper specification as required to obtain the polyamide-imide insulating coating. Its solid content is 31-33% (200 deg.C. times.2 hr. times.1.5 g) and viscosity is 7.50-12.5dPa.s (30 deg.C). The prepared polyamide-imide insulating paint comprises polyamide-imide, the molecular weight of the polyamide-imide is 21000-22000g/mol, and the structural formula is as follows:
the coatings prepared above were made into line samples, and the relevant parameters and test results are shown in table 1. The result shows that the polyamide-imide insulating paint prepared by the method has good insulating property and better heat resistance.
TABLE 1 coating-related Performance test results
Example 2
(1) At normal temperature, adding 500ml of N-methyl pyrrolidone into a reaction vessel, then adding 188.1g of MDA and 384g of TMA to heat the obtained mixed solution to 130 ℃ at the heating rate of 15-20 ℃/h for constant temperature reaction, carrying out azeotropic dehydration in the reaction process until the dehydration amount reaches over 85 wt% of the theoretical amount, sampling and detecting an infrared spectrogram of the reaction solution, and when an amino signal peak (a stretching vibration peak 3400-3500 cm--1) When the solution completely disappears, the temperature is reduced to below 50 ℃ to obtain an intermediate DIDC solution (incomplete dissolution).
(2) Adding 237.5g of MDI, 200ml of dimethyl succinate, 50ml of propylene carbonate and 4g of phase transfer catalyst benzyl trimethyl ammonium chloride into the solution obtained in the step (1), heating to 100 ℃ at the heating rate of 15-20 ℃/h again, reacting for 3h at constant temperature, then heating to 120 ℃ at the heating rate of 20 ℃/h for constant-temperature reaction, observing that the reaction solution is changed from turbid to transparent when the reaction generates carbon dioxide and obviously reduces, starting to detect the acid value, when the acid value is 6.4-7.2, 300ml of N, N-dimethylacetamide solvent is added, and then cooling to 75 ℃, adding 8g of ethanol, blocking unreacted isocyanate groups, stirring for 05h, then adding 400ml of N, N-dimethylformamide, 200ml of phenol and 350ml of No. 150 petroleum solvent, and adjusting to a proper specification as required to obtain the polyamide-imide insulating coating. Its solid content is 31-33% (200 deg.C. times.2 hr. times.1.5 g), viscosity is 7.5-12.5dPa.s (30 deg.C). The prepared polyamide-imide insulating paint comprises polyamide-imide, the molecular weight of the polyamide-imide is 22000-23000g/mol, and the structural formula is as follows:
comparative example
Adding 1000ml of N-methyl pyrrolidone, 300ml of xylene and 20g of isopropanol into a reaction vessel at normal temperature, then adding 530g of MDI and 384g of TMA, then heating to 95-100 ℃ at the heating rate of 15-20 ℃/h for constant temperature reaction for 2-3h, heating to 115-120 ℃ at the heating rate of 15-20 ℃/h for constant temperature reaction again until carbon dioxide generated by the reaction is obviously reduced, detecting the acid value, adding 400ml of N, N-dimethylformamide and 60g of benzyl methanol when the acid value is 6.4-7.2, sealing unreacted isocyanate groups, then cooling to 60-70 ℃, then adding 600ml of N-methyl pyrrolidone and 300ml of xylene, and adjusting to a proper specification as required to obtain the polyamide-imide insulating coating. Its solid content is 31-33% (200 deg.C. times.2 hr. times.1.5 g) and viscosity is 7.50-12.5dPa.s (30 deg.C).
The example 2 and the comparative example were prepared into line samples, and after being soaked in the refrigerant, the test results of the refrigerant are respectively shown in fig. 1a and b, and it can be seen from the figure that after the paint prepared by the method of the present invention is prepared into line samples, the surface of the material is smooth and bright under the soaking of the refrigerant, while the surface of the material of the comparative example is uneven and has dull gloss. The polyamide-imide insulating paint prepared by the invention has better refrigerant resistance.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A preparation method of a polyamide-imide insulating paint is characterized by comprising the following steps:
(1) dissolving 4,4' -diphenylmethane diamine and trimellitic anhydride in an amide organic solvent, heating to 125-130 ℃ at the speed of 15-20 ℃/h for reaction, and cooling to below 50 ℃ after the reaction is completed; wherein the molar ratio of the 4,4' -diphenylmethane diamine to trimellitic anhydride is 0.45-0.5: 1;
(2) reacting the product of the step (1) with diphenylmethane diisocyanate in an ester solvent under the action of a phase transfer catalyst, wherein the molar number of the diphenylmethane diisocyanate is the same as that of the 4,4' -diphenylmethane diamine in the step (1), the phase transfer catalyst is a quaternary ammonium salt or quaternary phosphonium salt phase transfer catalyst, and the reaction comprises
Heating to 95-100 ℃ at the heating rate of 15-20 ℃/h for constant temperature reaction for 2-3h, heating to 115-120 ℃ at the heating rate of 15-20 ℃/h for reaction, and adding a second organic solvent and an alcohol blocking agent to block unreacted isocyanate groups when the acid value of the reaction solution is 6.4-7.2;
(3) and (3) cooling the reaction liquid obtained in the step (2) to 60-70 ℃, and adding the amide organic solvent and the aromatic hydrocarbon diluent to obtain the polyamide-imide insulating coating.
2. The method of claim 1, wherein: in steps (1) and (3), the amide organic solvent includes one or more of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide and N, N-diethylformamide.
3. The method of claim 1, wherein: in the step (1), after the reaction is completed, the structural formula of the obtained product is as follows:
4. the method of claim 1, wherein: in the step (2), the phase transfer catalyst is selected from one or more of quaternary ammonium salt type phase transfer catalyst, quaternary phosphonium salt type phase transfer catalyst and polyethylene glycol.
5. The method for producing a fluoroacrylate according to claim 4, wherein: the quaternary ammonium salt catalyst comprises one or more of tetramethyl ammonium bromide, tetrabutyl ammonium bromide, benzyl trimethyl ammonium chloride, trioctylmethyl ammonium chloride and hexadecyl trimethyl ammonium bromide.
6. The method for producing a fluoroacrylate according to claim 4, wherein: the quaternary phosphonium salt phase transfer catalyst comprises one or more of triphenylethyl phosphonium bromide, tetraphenyl phosphonium chloride, benzyl triphenyl phosphonium bromide, benzyl triphenyl phosphonium chloride, tetraphenyl phosphonium bromide, tetra (diethylamino) phosphonium bromide, triphenyl butyl phosphonium bromide and triphenyl ethyl phosphonium bromide.
7. The method of claim 1, wherein: in the step (2), the ester solvent comprises one or more of dimethyl succinate, dimethyl glutarate, dimethyl adipate, diethyl succinate, diethyl adipate, gamma-butyrolactone and propylene carbonate, and the ratio of the ester solvent to the product of the step (1) is 150-: 1 mol.
8. The method of claim 1, wherein: in the step (2), when the acid value of the reaction solution is 6.4 to 7.2, the structural formula of the obtained product is as follows:
the molecular weight of the product was 15000-25000 g/mol.
9. The method of claim 1, wherein: the polyamide-imide insulating coating has a solid content of 31-33% and a viscosity of 7.50-12.5 dPa.s.
10. A polyamideimide insulating coating material prepared by the preparation method according to any one of claims 1 to 9, wherein: the polyamide-imide insulating paint comprises polyamide-imide, wherein the polyamide-imide comprises the following structural formula:
the molecular weight of the polyamideimide is 15000-25000 g/mol.
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2020
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Application publication date: 20200825 |