KR20160063464A - Soluble polyamide with high heat-resistance and producing method thereof - Google Patents
Soluble polyamide with high heat-resistance and producing method thereof Download PDFInfo
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- KR20160063464A KR20160063464A KR1020140166279A KR20140166279A KR20160063464A KR 20160063464 A KR20160063464 A KR 20160063464A KR 1020140166279 A KR1020140166279 A KR 1020140166279A KR 20140166279 A KR20140166279 A KR 20140166279A KR 20160063464 A KR20160063464 A KR 20160063464A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/02—Processes for applying liquids or other fluent materials performed by spraying
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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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
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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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
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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
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
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Abstract
More particularly, the present invention relates to a polyamide resin composition having heat resistance and solubility in a common solvent and a method of preparing the same, and more particularly, (Water, ethanol, DMSO, etc.) and having improved heat resistance and at the same time improved solubility in commercial solvents (water, ethanol, DMSO, etc.), and a process for producing the same.
According to the present invention as described above, there is an effect of providing a polyamide having heat resistance and solubility in a commercial solvent such as water, ethanol, DMSO and the like. In detail, the melting point of the polyamide made by the present invention is in the range of 165 to 175 DEG C, and it is relatively low in the polar solvent such as water, ethanol, DMSO, Of solubility. Therefore, it can be used as a coating agent by using such characteristics, and since it exhibits a solubility of more than enough to be used for a polar solvent such as water, it is possible to form a durable coating film while replacing the coating process using existing organic solvent, Can be applied as a functional coating agent in a field where a strong coating film of
Description
More particularly, the present invention relates to a polyamide resin composition having heat resistance and solubility in a common solvent and a method of preparing the same, and more particularly, (Water, ethanol, DMSO, etc.) and having improved heat resistance and at the same time improved solubility in commercial solvents (water, ethanol, DMSO, etc.), and a process for producing the same.
Polyamides are used in a wide variety of practical and industrial applications due to their inherent heat resistance, chemical resistance and physical properties. In general, polyamide is produced by polymerization reaction of diamine and diacid. Since polyamide is hardly dissolved in commercial solvent due to its excellent crystallinity, there is an inconvenience that organic solvent is used for various uses.
Efforts to use a polyamide resin as a coating material have been continuously tilted. The polyamide resin alone can satisfy the physical properties required as a coating material, for example, heat resistance, flexibility, gasoline resistance or oil resistance, In order to improve the productivity, a method of mixing additives such as a plasticizer, a nucleating agent, a heat resistant agent and the like or adjusting the processing temperature condition has been attempted to improve productivity. The addition of these additives increased the flexibility and other physical properties of the resin, but failed to satisfy both low-speed and high-speed productivity. In particular, the use of such additives in addition to organic solvents is detrimental to the working environment and difficult to treat waste in the future . Accordingly, there is a demand for development of a coating material that can improve productivity and improve environmental problems without deteriorating properties such as heat resistance and flexibility of the polyamide resin itself.
Korean Patent Laid-Open No. 10-2012-0078477 "Polyamide resin composition and molded article comprising the same" relates to a polyamide resin composition and a molded article comprising the same. According to this invention, polyamide resin N, N'- A mixture of 6-diyl bis [3- (3,5-di-t-butyl-4-hydroxyphenylpropionamide)] and tris (2,4-di- As a polyamide resin composition, there has been provided a polyamide resin composition and a molded article containing the polyamide resin composition, which exhibits very small changes in physical properties even when exposed to the external environment of oil and gasoline for a long time, and exhibits excellent productivity. However, tris (2,4-di-t-butylphenyl) phosphite had to be used as a crosslinking agent, and heat resistance and solubility were not sufficiently satisfied at the same time.
The inventors of the present invention prepared a polyamide having heat resistance and improved solubility in a commercial solvent such as water by appropriately mixing Tris (amine) and diamine with diacid to control the crystallinity of the polyamide. The melting point of the polyamide sold in the market is 210 to 220 ° C, which is excellent in heat resistance and hardly soluble in water and ethanol. The melting point of the polyamide prepared according to the present invention is 165-175 ° C., It has been confirmed that it has a solubility that is more than enough to be used as a coating agent in a commercial solvent such as water while maintaining heat resistance, and the invention is completed. Such highly heat-resistant and soluble polyamide resins can be usefully used as coatings in a variety of applications including tubes, moldings, sewing threads and filaments.
There is also a great environmental advantage that the coating process can be configured as a water-based system to reduce organic emissions, and there is a free amine group (free NH 2 ) to attach an additional reactor to the polyamide, .
An object of the present invention is to provide a polyamide resin having heat resistance and solubility in a common solvent. For this purpose, the ratio of Tris (amine) to diamine (amine) among carboxylic acids and amines, which are components for the polymerization reaction, is appropriately controlled to measure changes in heat resistance and solubility, , And to reduce the use of other cross-linking agents as much as possible, thereby reducing economic and environmental problems.
In order to achieve the above object, the present invention provides a polyamide polymer resin formed by a polymerization reaction of an amine and a carboxylic acid, wherein the polyamide polymer resin has a melting temperature of 150 to 180 ° C.
The amine may be a mixture comprising a triamine having three amine groups and a diamine having two amine groups.
The relative ratio of the Tris-amine to the diamine included in the mixture may be such that the molar ratio of the Tris-amine: diamine is from 25:75 to 10:90 have.
The polyamide polymer resin may be at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone (DMF), dimethylformamide (DMF), chloroform and DMSO The solubility in the mixed solvent may be 0.5% (weight / volume) or more.
The trisamine contained in the mixture may be tris (2-aminoethyl) amine.
The diamine contained in the mixture may be hexamethylene diamine.
The carboxylic acid may be undecanedioic acid.
Also, the present invention provides a high heat-resistant polymer coating liquid in which the polyamide polymer resin is dissolved in a solvent.
The solvent may be one or more solvents selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone, DMF, chloroform and DMSO.
The molar ratio of the carboxylic acid to the amine is 1: 1, and the molar ratio of the trisamine to the amine in the amine is 25:75 to 10: 90 to prepare a polyamide polymer resin formed by polymerization reaction; (2) The polyamide polymer resin is prepared by mixing at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone, DMF, chloroform and DMSO Preparing a high heat-resistant polymer coating solution by dissolving in a mixed solvent; And (3) coating the high heat-resistant polymer coating liquid on a surface to be coated and evaporating the solvent to dry the coating liquid.
According to the present invention as described above, there is an effect of providing a polyamide having heat resistance and solubility in a commercial solvent such as water, ethanol, DMSO and the like. In detail, the melting point of the polyamide made by the present invention is in the range of 165 to 175 DEG C, and it is relatively low in the polar solvent such as water, ethanol, DMSO, Of solubility. Therefore, it can be used as a coating agent by using such characteristics, and since it exhibits a solubility of more than enough to be used for a polar solvent such as water, it is possible to form a durable coating film while replacing the coating process using existing organic solvent, Can be applied as a functional coating agent in a field where a strong coating film of
1 is a schematic diagram showing a process of synthesizing a high heat-resistant soluble polyamide.
2 is an FT-IR analysis graph for confirming whether a high heat-resistant soluble polyamide is synthesized.
3 is a DSC analysis graph for high heat resistant soluble polyamide.
FIG. 4 is a graph of the change in melt temperature measured by varying the ratio of trisamine and diamine.
FIG. 5 is a photograph of a result of measuring the solubility of various high-heat-resistant soluble polyamides in various solvents.
FIG. 6 is a photograph of the result of measuring the solubility in various solvents by increasing the amount of the high heat-resistant soluble polyamide to 10% (weight / volume).
Hereinafter, the present invention will be described in detail.
The present invention provides a polyamide polymer resin formed by polymerization of an amine and a carboxylic acid, wherein the polyamide polymer resin has a melting temperature of 150 to 180 ° C. Tris-amine: When the molar ratio of the diamine is 25: 75, the melting temperature is 150 ° C. and the ratio of the tris-amine and the diamine is adjusted to 180 ° C. It was confirmed that the melting temperature rises. Preferably at a melting temperature of 160 DEG C or higher, the coating film of the polyamide polymer resin is robust.
The amine is a mixture comprising tris-amine having three amine groups and diamine having two amine groups. Other additives besides tris-amine and diamine may be added.
The relative ratio of the Tris-amine to the diamine included in the mixture is such that the molar ratio of the Tris-amine to the diamine is from 25:75 to 10:90 . Preferably, the molar ratio of the tris-amine to the diamine is 22: 78 to 18: 82, and the ratio of the trisamine to the diamine is 1: 4.
The polyamide polymer resin may be at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone, DMF (dimethyl formamide), chloroform and DMSO And a solubility in a mixed solvent of 0.5% (weight / volume) or more. The higher the solubility in the solvent is, the better the heat resistance is maintained.
The tris-amine contained in the mixture is characterized by being tris (2-aminoethyl) amine.
The diamine contained in the mixture is characterized by being hexamethylenediamine.
The carboxylic acid is undecanedioic acid.
In another aspect, the present invention provides a high heat-resistant polymer coating liquid in which the polyamide polymer resin is dissolved in a solvent.
Wherein the solvent is at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone, DMF, chloroform and DMSO (Dimethyl Sulfoxide) do.
In another aspect, the present invention relates to a process for preparing a polyamide resin composition comprising: (1) a molar ratio of a carboxylic acid and an amine of 1: 1; a molar ratio of a trisamine and a diamine in an amine of 25: To 10: 90, followed by preparing a polyamide polymer resin formed by polymerization reaction; (2) The polyamide polymer resin is prepared by mixing at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone, DMF, chloroform and DMSO Preparing a high heat-resistant polymer coating solution by dissolving in a mixed solvent; And (3) coating the high heat-resistant polymer coating liquid on a surface to be coated and evaporating the solvent to dry the coating liquid.
Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are merely illustrative of the present invention and that the scope of the present invention is not construed as being limited by these embodiments.
Example 1. High heat resistant polyamide synthesis
Overall, the synthesis of the high heat resistant polyamide was synthesized by the process of FIG. The high heat resistant polyamide was synthesized with diacid: Tren: diamine = 1: 0.2: 0.8, which satisfied both high heat resistance and solubility.
Specifically, 0.063 g (0.064 ml) of tris (2-aminoethyl) amine having a molecular weight of 0.977 g / mol, 0.2 g of hexamethylene diamine of 116.2 g / mol, 0.467 g of undecanedioic acid of 216.27 g / mol, methylpyrolidinone (15.98 ml) and triphenyl phosphite (0.76 ml) were placed in a 100 ml three-neck round bottom flask and stirred at 80 ° C under a nitrogen atmosphere for 3 hours.
Then, 420 ml of cold diethyl ether was added to precipitate 500 ml of the precipitated material. The precipitated material was collected through a vacuum filter, and the collected material was dried in a vacuum oven to synthesize a high heat resistant polyamide.
Experimental Example 1. Identification of high heat-resistant polyamide synthetics using FT-IR
2 is a graph showing the molecular structure analysis by Fourier transform infrared spectroscopy (FT-IR, JASCO FT / IR 4100) to confirm whether or not the high heat resistant polyamide was synthesized with respect to the material synthesized in Example 1. FIG. And a characteristic peak for a wavelength of 4000-400 cm -1 was detected.
The FT-IR peak characteristic of the polyamide is 3300 to 3250 cm -1 (Amide A), 3100 to 3050 cm -1 (Amide B), 1650 to 1600 cm -1 (Amide I, C = -1 (AmideI I, CN stretching and CO-NH bending), respectively.
The high heat-resistant polyamide synthesized has functional groups that can cause CN stretching, CO-NH bending, C = O stretching, CH stretching and CH stretching.
Experimental Example 2 Characterization of high heat-resistant polyamide synthetics using DSC analysis
3 is a graph showing the thermal characteristics of the high heat resistant polyamide synthesized in Example 1 by a differential scanning calorimeter (DSC,
Differential scanning calorimetry (DSC) is a device for measuring the difference in heat flux generated from a sample by applying the same temperature program to the sample and inert reference material. The heat flux is equivalent to the conducted power and is usually measured in watts (W) or milliwatts (mW). When heat flux or conduction power is differentiated by time, it is converted into energy amount and expressed as mW / s or mJ. The conducted energy corresponds to the change in enthalpy of the sample, and when the sample absorbs the energy, the enthalpy change is called endothermic. The rising peak is an exothermic reaction and the falling peak is an endothermic reaction based on the DSC value of 0.
Referring to FIG. 3, it can be seen that a peak whose value changes abruptly in the second run of the DSC value is formed at 160 to 180 ° C. This peak is an endothermic reaction and the temperature at this point is the melting point of the high heat-resistant polyamide.
In the polymer resin, the melting point temperature is a temperature at which the transition from the solid state to the fluid liquid state is started, and the temperature at which the flow of the crystalline portion starts. The thermoplastic resin becomes flexible as the temperature rises. When the temperature is raised above a certain temperature, the flow starts and the viscosity decreases. This indicates that due to the elevated temperature, the kinetic energy of the molecules in the resin increases and flows along with the volume change due to the distance between the polymer chains being distant.
Experimental Example 3. Change of Melting Point with Variation of Polymerization Ratio
In order to make the polyamide having both high heat resistance and solubility, the change of the melting temperature (Tm) was measured by varying the ratio of tris (2-aminoethyl) amine: diamine reacted with diacid (see FIG. In the X-axis, the number before tris (2-aminoethyl) amine is the number after diamine and the sum is 1.
FIG. 4 shows that the melting point (Tm) increases as the ratio of tris (2-aminoethyl) amine decreases and the melting temperature (melting point) hardly changes or slightly decreases as the ratio exceeds 0.2: 0.8 . Therefore, a ratio of 0.2: 0.8 is suitable for maximizing the melting temperature.
Experimental Example 4. Changes in Solubility with Variation of Polymerization Ratio
When the relative ratio of tris (2-aminoethyl) amine to diamine is varied, the higher the ratio of tris (2-aminoethyl) amine, the lower the solubility. Therefore, we confirmed the degree of solubility of the polyamide polymerized with diacid with a ratio of tris (2-aminoethyl) amine: diamine of 0.2: 0.8.
The ratio of diacid: tris (2-aminoethyl) amine: diamine to acetone, ethanol, N-methyl-2-pyrrolidone (DMF), dimethyl formamide (DMF), and dimethyl sulfoxide (DMSO) The high heat-resistant polyamide was dissolved in 0.5% (weight / volume) to observe dissolution (see FIG. 5).
5, it was confirmed that the tested high-heat-resistant polyamide was soluble in 0.5% (weight / volume) or more of polar solvents such as distilled water and polar solvents such as ethanol and non-polar solvents.
The ratio of diacid: tris (2-aminoethyl) amine: diamine to distilled water, ethanol, DMSO (dimethyl sulfoxide) and NMP (N-methyl-2-pyrrolidone) was measured to increase the amount of solute. (Weight / volume) ratio by adding 100 mg per 1 ml of the high heat-resistant polyamide polymerized in the ratio of 1: 0.2: 0.8, and dissolving was conducted by magnetic steering for 36 hours (see FIG.
6, it was confirmed that a significant amount was dissolved in a) distilled water, b) ethanol, c) DMSO and d) NMP solvent, and relatively yellowish and transparent color was dissolved in DMSO and NMP solvent, Distilled water and ethanol solvent showed opaque white color. It is believed that it dissolves in distilled water and ethanol solvent to maximum solubility and then dispersed in colloidal form in solvent. Viscosity is high when dissolved in ethanol solvent and lowest when dissolved in distilled water. As a result, it was confirmed that even polar solvents such as distilled water and ethanol were soluble in a solubility of 0.5% (weight / volume) or more, and in a solvent such as DMSO or NMP, it was dissolved in a solubility of 10% (weight / volume) or more. As the solubility is about this level, it can be utilized as a coating agent.
Having described specific portions of the present invention in detail, it will be apparent to those skilled in the art that this specific description is only a preferred embodiment and that the scope of the present invention is not limited thereby. It will be obvious. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.
Claims (10)
A polyamide polymer resin having a melting temperature of 150 to 180 ° C.
A polyamide polymer resin characterized in that it is a mixture comprising a triamine having three amine groups and a diamine having two amine groups.
Wherein the molar ratio of the tris-amine to the diamine is from 25:75 to 10:90.
Solubility in at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone (DMF), dimethylformamide (DMF), chloroform and dimethylsulfoxide (DMSO) / Volume) of the polyamide polymer resin.
Wherein the polyamide resin is tris (2-aminoethyl) amine.
Wherein the polyamide resin is hexamethylenediamine.
A polyamide polymer resin characterized by being undecanedioic acid.
Wherein the solvent is at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone, DMF (Dimethyl Formamide), chloroform and DMSO Coating liquid.
(2) The polyamide polymer resin is prepared by mixing at least one solvent selected from the group consisting of water, ethanol, acetone, N-methyl-2-pyrrolidone, DMF, chloroform and DMSO Preparing a high heat-resistant polymer coating solution by dissolving in a mixed solvent; And
(3) coating the high heat-resistant polymer coating liquid on a surface to be coated and evaporating the solvent to dry the coating liquid.
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