CN111533891B - Polyester polyol for high-temperature-resistant adhesive and preparation method thereof - Google Patents
Polyester polyol for high-temperature-resistant adhesive and preparation method thereof Download PDFInfo
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- CN111533891B CN111533891B CN202010298505.6A CN202010298505A CN111533891B CN 111533891 B CN111533891 B CN 111533891B CN 202010298505 A CN202010298505 A CN 202010298505A CN 111533891 B CN111533891 B CN 111533891B
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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Abstract
The invention relates to polyester polyol for a high-temperature-resistant adhesive, which is prepared from the following raw materials in percentage by weight: 40-45% phthalic anhydride; 15-25% unsaturated fatty acids; 30-35% of dihydric alcohol; 3-8% of trihydric alcohol; 5-10% of amide organic solvent; and 0.01-0.05% of catalyst. The application also relates to a preparation method of the polyester polyol for the high-temperature-resistant adhesive. The polyester polyol for the high-temperature-resistant adhesive has a simple preparation process, and the adhesive prepared from the polyester polyol can resist the temperature of 230 ℃ and has high curing speed.
Description
Technical Field
The invention relates to the technical field of polyester polyol and adhesives, in particular to polyester polyol for a high-temperature-resistant adhesive and a preparation method thereof.
Background
Currently, adhesives for the door industry use waste polyester bottles or waste polyester yarns as raw materials to produce adhesives. On one hand, the raw material sources, the waste polyester bottles, the waste silk and the like belong to renewable resources, have certain value and are higher in collection cost. On the other hand, many of the existing adhesives for door industry have unstable hydroxyl value, poor binding power, long curing time and no high temperature resistance, and influence the yield and quality of products.
Therefore, there is a continuing need in the art to develop a polyester polyol for a high temperature resistant adhesive that can be used to prepare adhesives that are resistant to high temperatures and have good adhesion, and a method for preparing the same.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide the polyester polyol for the high-temperature-resistant adhesive, which can be used for preparing the adhesive with high temperature resistance and good bonding force.
The application also aims to provide a preparation method of the polyester polyol for the high-temperature-resistant adhesive.
In order to achieve the object of the present invention, the present application provides the following technical solutions.
In a first aspect, the present application provides a polyester polyol for a high temperature resistant adhesive, wherein the polyester polyol for a high temperature resistant adhesive is prepared from raw materials, and the raw materials comprise the following components by weight:
40-45% phthalic anhydride;
15-25% unsaturated fatty acids;
30-35% of dihydric alcohol;
3-8% of trihydric alcohol;
5-10% of amide organic solvent; and
0.01-0.05% of catalyst.
In one embodiment of the first aspect, the hydroxyl value of the polyester polyol for the high temperature resistant adhesive is 40-50mgKOH/g, which is determined by HG/T2709-1995 polyester polyol hydroxyl value determination method; an acid value of 5mgKOH/g or less as determined by the HG/T2708-1995 polyester polyol acid value determination method; and a viscosity at 25 ℃ of 50000 to 100000 mPas, measured by the GB/T2794-1995 rotational viscometer method.
In a second aspect, the present application provides a method for preparing the polyester polyol for the high temperature resistant adhesive according to the first aspect, wherein the method comprises the following steps:
s1: mixing phthalic anhydride, unsaturated fatty acid, dihydric alcohol and trihydric alcohol under the protection of inert gas, heating to dissolve the materials, heating to a first reaction temperature, and keeping for a first preset time period to obtain a first reaction mixture;
s2: adding a catalyst into the first reaction mixture under the protection of inert gas, then heating to a second reaction temperature, and keeping for a second preset time period to obtain a second reaction mixture;
s3: detecting the acid value of the second reaction mixture, when the acid value is less than or equal to 20mgKOH/g, cooling to 220-230 ℃, starting vacuum dehydration, keeping the vacuum degree from minus 0.01MPa to minus 0.09MPa, sampling and detecting the acid value after vacuum treatment is carried out for 1-2 hours, and stopping vacuum when the acid value is less than or equal to 5mgKOH/g, thus obtaining a third reaction mixture;
s4: under the protection of inert gas, cooling to 130-140 ℃, adding an amide organic solvent into the third reaction mixture, and stirring for 0.5-1 hour to obtain polyester polyol for the high-temperature-resistant adhesive;
wherein, in the step S1, the first reaction temperature is 180-200 ℃, and the first preset time period is 2-4 hours;
wherein, in step S2, the second reaction temperature is 220-240 ℃, and the second predetermined time period is 3-5 hours.
Compared with the prior art, the polyester polyol for the high-temperature-resistant adhesive has the beneficial effects that the preparation process of the polyester polyol is simple, the adhesive prepared by using the polyester polyol can resist the temperature of 230 ℃, the curing speed is high, and the polyester polyol is suitable for the operation needing rapid curing, such as door plate pressing in flow line production.
Drawings
FIG. 1 shows FTIR spectra of polyester polyols for high temperature resistant adhesive in accordance with example 1.
Detailed Description
Unless otherwise indicated, implied from the context, or customary in the art, all parts and percentages herein are by weight and the testing and characterization methods used are synchronized with the filing date of the present application. Where applicable, the contents of any patent, patent application, or publication referred to in this application are incorporated herein by reference in their entirety, and the equivalent family of patents is also incorporated by reference, in particular for the definitions set forth in these documents regarding synthetic techniques, product and process designs, polymers, comonomers, initiators or catalysts, and the like, in the art. To the extent that a definition of a particular term disclosed in the prior art is inconsistent with any definitions provided herein, the definition of the term provided herein controls.
The numerical ranges in this application are approximations, and thus may include values outside of the ranges unless otherwise specified. A numerical range includes all numbers from the lower value to the upper value, in increments of 1 unit, provided that there is a separation of at least 2 units between any lower value and any higher value. For example, if a compositional, physical, or other property (e.g., molecular weight, melt index, etc.) is recited as 100 to 1000, it is intended that all individual values, e.g., 100, 101,102, etc., and all subranges, e.g., 100 to 166,155 to 170,198 to 200, etc., are explicitly recited. For ranges containing values less than 1 or fractions greater than 1 (e.g., 1.1,1.5, etc.), then 1 unit is considered to be 0.0001,0.001,0.01 or 0.1, as appropriate. For ranges containing single digit numbers less than 10 (e.g., 1 to 5), 1 unit is typically considered 0.1. These are merely specific examples of what is intended to be expressed and all possible combinations of numerical values between the lowest value and the highest value enumerated are to be considered to be expressly stated in this application. The numerical ranges within this application provide, among other things, the amount of each comonomer in the acrylate copolymer, the amount of each component in the photoresist composition, the temperature at which the acrylate is synthesized, and the various characteristics and properties of these components.
When used with respect to a chemical compound, the singular includes all isomeric forms and vice versa (e.g., "hexane" includes all isomers of hexane, individually or collectively) unless explicitly stated otherwise. In addition, unless explicitly stated otherwise, the use of the terms "a", "an" or "the" are intended to include the plural forms thereof.
The terms "comprising," "including," "having," and derivatives thereof do not exclude the presence of any other component, step or procedure, and are not intended to exclude the presence of other elements, steps or procedures not expressly disclosed herein. To the extent that any doubt is eliminated, all compositions herein containing, including, or having the term "comprise" may contain any additional additive, adjuvant, or compound, unless expressly stated otherwise. Rather, the term "consisting essentially of … …" excludes any other components, steps or processes from the scope of any such term as are hereinafter recited, out of those necessary for performance. The term "consisting of … …" does not include any components, steps or processes not specifically described or listed. Unless explicitly stated otherwise, the term "or" refers to the listed individual members or any combination thereof.
In one embodiment, the present application provides in a first aspect a polyester polyol for a high temperature resistant adhesive, wherein the polyester polyol for a high temperature resistant adhesive is prepared from raw materials, and the raw materials comprise the following components in percentage by weight:
40-45% phthalic anhydride;
15-25% unsaturated fatty acids;
30-35% of dihydric alcohol;
3-8% of trihydric alcohol;
5-10% of amide organic solvent; and
0.01-0.05% of catalyst.
In one embodiment, the raw material for preparing the polyester polyol for the high temperature resistant adhesive may include, on a weight percentage basis, 40%, 40.5%, 41%, 41.5%, 42%, 42.5%, 43%, 43.5%, 44%, 44.5%, 45% or phthalic anhydride within a range or sub-range between any two of them.
In one embodiment, the unsaturated fatty acid is oleic acid. Oleic acid can react with diethylene glycol to produce diethylene glycol dioleate, which is a low viscosity ester and can well reduce the viscosity of polyester. In one embodiment, the raw material for preparing the polyester polyol for the high temperature resistant adhesive may include, on a weight percentage basis, 15%, 15.5%, 16%, 16.5%, 17%, 17.5%, 18%, 18.5%, 19%, 19.5%, 20%, 20.5%, 21%, 21.5%, 22%, 22.5%, 23%, 23.5%, 24%, 24.5%, 25% or unsaturated fatty acid within a range or sub-range between any two values thereof.
In one embodiment, the glycol may be diethylene glycol or triethylene glycol. In one embodiment, the polyester polyol used to prepare the high temperature resistant adhesive may include 30%, 30.5%, 31%, 31.5%, 32%, 32.5%, 33%, 34%, 34.5%, 35% or any range or subrange therebetween of diol by weight percent.
In one embodiment, the triol may be glycerol. In one embodiment, the polyester polyol used to prepare the high temperature resistant adhesive may include 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, or any range or subrange therebetween, of a triol, on a weight percent basis.
In one embodiment, the amide-based organic solvent may be dimethylformamide or dimethylacetamide. Amide organic solvents can be used to reduce the viscosity of the polyester. In one embodiment, the raw material for preparing the polyester polyol for the high temperature resistant adhesive may include 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10% or the amide-based organic solvent within a range or sub-range between any two values of the above-mentioned raw materials.
In one embodiment, the catalyst may be an organotin-based catalyst or an alkyl titanate-based catalyst commonly used in the art. In one embodiment, the catalyst may be dioctyltin dilaurate or dibutyltin dilaurate. In one embodiment, the catalyst may be tetrabutyl titanate. In one embodiment, the raw material for preparing the polyester polyol for the high temperature resistant adhesive may include 0.01%, 0.02%, 0.03%, 0.04%, 0.05% or the catalyst within a range or sub-range between any two values of the above on a weight percentage basis.
In a second aspect, the present application provides a method for preparing polyester polyol for high temperature resistant adhesive, as described in the first aspect, wherein the method comprises the following steps:
s1: mixing phthalic anhydride, unsaturated fatty acid, dihydric alcohol and trihydric alcohol under the protection of inert gas, heating to dissolve the materials, heating to a first reaction temperature, and keeping for a first preset time period to obtain a first reaction mixture;
s2: adding a catalyst into the first reaction mixture under the protection of inert gas, then heating to a second reaction temperature, and keeping for a second preset time period to obtain a second reaction mixture;
s3: detecting the acid value of the second reaction mixture, when the acid value is less than or equal to 20mgKOH/g, cooling to 220-230 ℃, starting vacuum dehydration, keeping the vacuum degree from minus 0.01MPa to minus 0.09MPa, sampling and detecting the acid value after vacuum treatment is carried out for 1-2 hours, and stopping vacuum when the acid value is less than or equal to 5mgKOH/g, thus obtaining a third reaction mixture;
s4: under the protection of inert gas, cooling to 130-140 ℃, adding an amide organic solvent into the third reaction mixture, and stirring for 0.5-1 hour to obtain polyester polyol for the high-temperature-resistant adhesive;
wherein, in the step S1, the first reaction temperature is 180-200 ℃, and the first preset time period is 2-4 hours;
wherein, in step S2, the second reaction temperature is 220-240 ℃, and the second predetermined time period is 3-5 hours.
In one embodiment, in step S3, the vacuum is gradually increased. The conversion rate can be effectively improved and the acid value of the polyester polyol can be reduced by gradually increasing the vacuum degree. In a preferred embodiment, said gradually increasing the vacuum comprises increasing the vacuum from-0.01 MPa to-0.03 MPa in 30 minutes; the vacuum degree is improved from-0.03 MPa to-0.05 MPa within 30 minutes; the vacuum degree is improved from-0.05 MPa to-0.07 MPa within 30 minutes; the vacuum was increased from-0.07 MPa to-0.09 MPa within 30 minutes.
Examples
The following will describe in detail the embodiments of the present invention, which are implemented on the premise of the technical solution of the present invention, and the detailed embodiments and the specific operation procedures are given, but the scope of the present invention is not limited to the following embodiments.
Example 1
The embodiment provides a preparation method of polyester polyol for a high temperature resistant adhesive, which comprises the following steps:
s1: under the protection of nitrogen, mixing 4000kg of phthalic anhydride, 1500kg of oleic acid, 3495kg of diethylene glycol and 300kg of glycerol, heating to dissolve the materials, heating to 180-200 ℃, and preserving heat for 2-4 hours to obtain a first reaction mixture;
s2: under the protection of inert gas, adding 5kg of dibutyltin dilaurate into the first reaction mixture, then heating to 220-240 ℃, and preserving heat for 3-5 hours to obtain a second reaction mixture;
s3: detecting the acid value of the second reaction mixture, when the acid value is less than or equal to 20mgKOH/g, cooling to 220-230 ℃, starting vacuum dehydration, gradually increasing the vacuum degree, keeping the vacuum degree between-0.01 MPa and-0.09 MPa, sampling to detect the acid value after 1-2 hours of vacuum, and when the acid value is less than or equal to 5mgKOH/g, stopping vacuum to obtain a third reaction mixture;
s4: and under the protection of inert gas, cooling to 130-140 ℃, adding 700kg of dimethylformamide into the third reaction mixture, and stirring for 0.5-1 hour to obtain 9115kg of polyester polyol for the high-temperature-resistant adhesive.
The step-wise raising of the vacuum in step S3 comprises raising the vacuum from-0.01 MPa to-0.03 MPa within 30 minutes; the vacuum degree is improved from-0.03 MPa to-0.05 MPa within 30 minutes; the vacuum degree is improved from minus 0.05MPa to minus 0.07MPa within 30 minutes; the vacuum degree is increased from-0.07 MPa to-0.09 MPa within 30 minutes.
The FTIR spectrum of the polyester obtained in this example 1 is shown in FIG. 1. Referring to FIG. 1, 3439cm -1 An infrared characteristic absorption peak which may be a hydrogen-oxygen bond; 3071cm -1 、1599cm -1 -1487cm -1 、705cm -1 Possibly an infrared characteristic absorption peak of the benzene ring; 2952cm -1 -2876cm -1 、1449cm -1 -1377cm -1 And 941cm -1 -746cm -1 An infrared characteristic absorption peak which may be a carbon-hydrogen bond; 1727cm -1 -1671cm -1 Possibly a characteristic infrared absorption peak of the carbon-oxygen double bond. By comprehensive analysis, the main component of the polyester polyol for the high temperature resistant adhesive of the present embodiment may be diethyl phthalate.
The hydroxyl value of the polyester polyol for the high-temperature-resistant adhesive is 40mgKOH/g, and is determined by a method for determining the hydroxyl value of the polyester polyol by HG/T2709-1995; the acid value is 3.0mgKOH/g, and is determined by an HG/T2708-1995 polyester polyol acid value determination method; and a viscosity of 50000 mPas at 25 ℃ as measured by a GB/T2794-1995 rotational viscometer.
Example 2
The embodiment provides a preparation method of polyester polyol for a high temperature resistant adhesive, which comprises the following steps:
s1: under the protection of nitrogen, 4500kg of phthalic anhydride, 1500kg of oleic acid, 3000kg of triethylene glycol and 500kg of glycerol are mixed, heated to be dissolved, heated to 180-200 ℃, and kept warm for 2-4 hours to obtain a first reaction mixture;
s2: under the protection of inert gas, adding 1kg of tetrabutyl titanate into the first reaction mixture, then heating to 220-240 ℃, and preserving heat for 3-5 hours to obtain a second reaction mixture;
s3: detecting the acid value of the second reaction mixture, when the acid value is less than or equal to 20mgKOH/g, cooling to 220-230 ℃, starting vacuum dehydration, gradually increasing the vacuum degree, keeping the vacuum degree between-0.01 MPa and-0.09 MPa, sampling to detect the acid value after 1-2 hours of vacuum, and when the acid value is less than or equal to 5mgKOH/g, stopping vacuum to obtain a third reaction mixture;
s4: and under the protection of inert gas, cooling to 130-140 ℃, adding 499kg of dimethylformamide into the third reaction mixture, and stirring for 0.5-1 hour to obtain 9095kg of polyester polyol for the high-temperature-resistant adhesive.
The step-by-step vacuum degree increase in the step S3 comprises increasing the vacuum degree from-0.01 MPa to-0.03 MPa within 30 minutes; the vacuum degree is improved from-0.03 MPa to-0.05 MPa within 30 minutes; the vacuum degree is improved from minus 0.05MPa to minus 0.07MPa within 30 minutes; the vacuum degree is increased from-0.07 MPa to-0.09 MPa within 30 minutes.
The hydroxyl value of the polyester polyol for the high-temperature-resistant adhesive is 50mgKOH/g, and the hydroxyl value is determined by a determination method of the hydroxyl value of the polyester polyol of HG/T2709-1995; the acid value is 3.5mgKOH/g, and is determined by an HG/T2708-1995 polyester polyol acid value determination method; and a viscosity of 50000 mPas at 25 ℃ as measured by a GB/T2794-1995 rotational viscometer.
Effects of the embodiment
Example 3
The present effect example relates to the preparation of an adhesive and the performance test thereof using the polyester polyol for a high temperature resistant adhesive synthesized in example 1.
The experimental procedure for this effect was as follows: 90kg of the polyester polyol for a high-temperature-resistant adhesive synthesized in example 1, 175kg of methylene chloride, 0.01kg of dimorpholinodiethyl ether, 0.03kg of dibutyltin dilaurate and 5kg of natural rosin resin were put into a stirred tank and stirred uniformly, and then 45kg of crude isocyanate MDI was added thereto with stirring and stirred for 30 minutes to obtain an adhesive according to example 3.
The adhesive according to example 3 was evaluated for adhesion and adhesion after aging in the following manner.
And (3) testing the adhesive force: a group 3 of metal bonds were made using the adhesive of example 3 and after curing at room temperature for 72 hours, the bonds were stretched using a tensile machine and the force to break was recorded.
Testing the adhesion force after aging: three groups of metal workpieces were prepared using the adhesive of example 3, and aged at 230 ℃ for half an hour, then cured at room temperature for 72 hours, stretched with a tensile machine, and the tensile fracture force was recorded, and the results of the specific test of the adhesive after aging are shown in table 1 below.
TABLE 1 Performance test results for Adhesives according to example 3
From the above table 1, it can be seen that the adhesive prepared from the polyester polyol for the high temperature resistant adhesive described herein has significantly improved adhesion and adhesion after aging, and is more suitable for door industry.
The embodiments described above are intended to facilitate the understanding and appreciation of the application by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present application is not limited to the embodiments herein, and those skilled in the art who have the benefit of this disclosure will appreciate that many modifications and variations are possible within the scope of the present application without departing from the scope and spirit of the present application.
Claims (5)
1. The polyester polyol for the high-temperature-resistant adhesive is characterized by being prepared from the following raw materials in percentage by weight:
40% phthalic anhydride;
15% unsaturated fatty acid;
34.95% glycol;
3% of a trihydric alcohol;
7% of amide organic solvent; and
0.05% of a catalyst;
wherein the unsaturated fatty acid is oleic acid;
the amide organic solvent is dimethylformamide or dimethylacetamide;
the catalyst is an organic tin catalyst; the dihydric alcohol comprises diethylene glycol and/or triethylene glycol;
the trihydric alcohol comprises glycerol;
the hydroxyl value of the polyester polyol for the high-temperature-resistant adhesive is 40mgKOH/g, and the hydroxyl value is determined by an HG/T2709-1995 polyester polyol hydroxyl value determination method; the acid value is 3.0mgKOH/g, and is determined by an HG/T2708-1995 polyester polyol acid value determination method; and a viscosity of 50000 mPas at 25 ℃ as measured by a GB/T2794-1995 rotational viscometer.
2. The polyester polyol according to claim 1, wherein the organotin catalyst comprises dioctyltin dilaurate or dibutyltin dilaurate.
3. A method for preparing polyester polyol for high temperature resistant adhesive according to any one of claims 1-2, wherein the method comprises the following steps:
s1: mixing phthalic anhydride, unsaturated fatty acid, dihydric alcohol and trihydric alcohol under the protection of inert gas, heating to dissolve the materials, heating to a first reaction temperature, and keeping for a first preset time period to obtain a first reaction mixture;
s2: adding a catalyst into the first reaction mixture under the protection of inert gas, then heating to a second reaction temperature, and keeping for a second preset time period to obtain a second reaction mixture;
s3: detecting the acid value of the second reaction mixture, when the acid value is less than or equal to 20mgKOH/g, cooling to 220-230 ℃, starting vacuum dehydration, keeping the vacuum degree from minus 0.01MPa to minus 0.09MPa, after vacuum treatment for 1-2 hours, sampling to detect the acid value, when the acid value is less than or equal to 5mgKOH/g, stopping vacuum to obtain a third reaction mixture;
s4: under the protection of inert gas, cooling to 130-140 ℃, adding an amide organic solvent into the third reaction mixture, and stirring for 0.5-1 hour to obtain polyester polyol for the high-temperature-resistant adhesive;
wherein, in the step S1, the first reaction temperature is 180-200 ℃, and the first preset time period is 2-4 hours;
wherein, in step S2, the second reaction temperature is 220-240 ℃, and the second predetermined time period is 3-5 hours.
4. The production method according to claim 3, wherein in step S3, the degree of vacuum is gradually raised.
5. The method of claim 4, wherein said gradually raising the vacuum comprises raising the vacuum from-0.01 MPa to-0.03 MPa in 30 minutes; the vacuum degree is improved from-0.03 MPa to-0.05 MPa within 30 minutes; the vacuum degree is improved from minus 0.05MPa to minus 0.07MPa within 30 minutes; the vacuum degree is increased from-0.07 MPa to-0.09 MPa within 30 minutes.
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