CN109266296B - Anaerobic structural adhesive and preparation method thereof - Google Patents
Anaerobic structural adhesive and preparation method thereof Download PDFInfo
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- CN109266296B CN109266296B CN201810955316.4A CN201810955316A CN109266296B CN 109266296 B CN109266296 B CN 109266296B CN 201810955316 A CN201810955316 A CN 201810955316A CN 109266296 B CN109266296 B CN 109266296B
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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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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
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Abstract
The invention provides an anaerobic adhesive structural adhesive and a preparation method thereof, wherein the anaerobic adhesive comprises the following components: the self-made polyurethane acrylic oligomer, the hydroxyl acrylate monoester, the thickening agent, the polymerization inhibitor, the accelerator, the metal ion chelating agent, the auxiliary accelerator and the initiator. The polyurethane acrylic oligomer is synthesized by 15-25 parts of liquid methacrylate, 5-15 parts of solid bisphenol compounds, 5-25 parts of diisocyanate monomers, 0.02-0.10 part of catalyst, 20-50 parts of polyether glycol and 5-20 parts of liquid hydroxyl acrylate monoester compounds. The anaerobic adhesive has the advantages of large filling gap, high curing speed, high impact strength and shear strength, excellent water resistance, temperature resistance and medium resistance, can be used for structural bonding, flange plate sealing and the like of various metal materials, and is particularly suitable for flange surface sealing and metal part bonding with high temperature, large vibration and medium corrosion.
Description
Technical Field
The invention relates to the field of adhesives, in particular to an anaerobic structural adhesive and a preparation method thereof.
Background
The anaerobic adhesive is called anaerobic adhesive for short, is a single-component sealing adhesive prepared by utilizing the principle of oxygen-to-free radical polymerization inhibition, can be rapidly polymerized and cured at room temperature under the condition that a coating surface is isolated from air and catalyzed, and can be used for bonding and sealing. The anaerobic adhesive is a multi-component mixed system, which is prepared by mixing acrylate, acrylate oligomer and the like serving as main resin with the raw materials of an accelerator, an auxiliary accelerator, a polymerization inhibitor, an initiator and the like, and can also be added with other additives such as a filler, a dye, a pigment, a thickening agent, a thixotropic agent and the like according to needs. The anaerobic adhesive has unique anaerobic adhesive curing characteristic, and can be applied to the aspects of locking, sealing, fixing, bonding, leaking stoppage and the like. The anaerobic adhesive becomes an indispensable adhesive variety in the mechanical industry, and has wide application in the industries of aerospace, war industry, automobiles, machinery, electronics, electricity and the like.
According to the literature, the main anaerobic adhesives on the market at present are mainly classified into the following two types: the monomer has good temperature resistance, medium resistance and high bonding strength, but has poor impact toughness; the acrylic carbamate product formed by the reaction of isocyanate, hydroxyl methacrylate and polyol has good low temperature resistance and impact resistance, but has low strength and poor medium resistance, and particularly the acid and alkali resistance is not as good as that of epoxy type.
The invention discloses an anaerobic adhesive which is prepared by taking a self-made and synthesized bifunctional polyurethane acrylic acid oligomer as main resin and mixing the main resin with other components. The preparation method of the oligomer has the characteristics of easily obtained raw materials, simple synthesis steps, controllable process, high product stability and the like, the anaerobic adhesive prepared from the oligomer can integrate the advantages of the two types of anaerobic adhesives on the market, can overcome the defects of the two types of anaerobic adhesives, has the advantages of high curing speed, high filling gap, high shear strength, high impact strength, high water resistance, high temperature resistance, high medium resistance and the like, can be used for structural bonding of metals such as steel, copper, iron and the like, and sealing of a flange plate with high temperature and high vibration, or is matched with a small amount of accelerant to be used for structural bonding of metals such as glass, plastics and electroplated layers.
Disclosure of Invention
The invention aims to provide an anaerobic adhesive structural adhesive and a preparation method thereof.
In order to achieve the purpose of the invention, the following solutions are specifically adopted: the anaerobic adhesive comprises the following components in parts by mass:
70-95 parts of self-made polyurethane acrylic oligomer;
2-10 parts of a hydroxyl acrylate monoester;
0-4 parts of a thickening agent;
0.02-0.20 part of polymerization inhibitor;
0.5-1.5 parts of an accelerator;
0.1-0.5 part of metal ion chelating agent;
0.5-1.5 parts of an auxiliary accelerator;
1.0-3 parts of an initiator.
The polyurethane acrylic acid oligomer used in the invention is synthesized by the following raw materials: 15 to 25 parts of liquid methacrylate, 5 to 15 parts of solid bisphenol compound, 5 to 25 parts of diisocyanate monomer, 0.02 to 0.10 part of catalyst, 20 to 50 parts of polyether glycol and 5 to 20 parts of liquid hydroxyl acrylate monoester compound. The preparation method comprises the following steps:
(1) the oligomer preparation needs a closed reaction kettle, needs dry nitrogen and ensures that the temperature in the kettle can be accurately controlled;
(2) adding liquid methacrylate into the kettle, then adding the solid bisphenol compound into the liquid methacrylate, heating to 20-30 ℃, and stirring until the solid bisphenol compound is completely dissolved;
(3) adding a diisocyanate monomer and a catalyst, introducing dry nitrogen for protection, heating to 45-55 ℃, and carrying out heat preservation reaction for 1-3 h;
(4) adding polyether glycol, introducing dry nitrogen for protection, heating to 65-75 ℃, and reacting for 1-3 h under heat preservation;
(5) adding a liquid hydroxyl acrylate monoester compound, introducing dry nitrogen for protection, keeping the temperature at 65-75 ℃, and stirring for reaction for 0.5-1.5 hours;
(6) cooling to normal temperature, and discharging to obtain the polyurethane acrylic acid oligomer.
More specifically, the solid bisphenol compound selected in the preparation method of the polyurethane acrylic oligomer can be bisphenol A, hydrogenated bisphenol A and the like, the liquid methacrylate can be ethyl methacrylate, isobornyl methacrylate and the like, the diisocyanate monomer can be toluene diisocyanate, diphenylmethane diisocyanate and the like, the polyether diol can be polytetrahydrofuran diol with molecular weight of 2000 or polypropylene glycol with molecular weight of 2000, and the liquid hydroxyl acrylate monoester can be hydroxyethyl methacrylate and hydroxypropyl methacrylate.
More specifically, the hydroxy acrylate monoester used for preparing the anaerobic adhesive can be selected from hydroxymethyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate and the like, preferably hydroxyethyl methacrylate;
the accelerator used by the anaerobic adhesive is N, N-dimethyl-p-toluidine, N-diethyl-p-toluidine, acetyl phenylhydrazine and the like, preferably acetyl phenylhydrazine;
the polymerization inhibitor used by the anaerobic adhesive is 1, 4-naphthoquinone, 1, 4-benzoquinone, hydroquinone and the like, preferably 1, 4-benzoquinone;
the auxiliary accelerator used in the anaerobic adhesive is saccharin; the chelating agent used by the anaerobic adhesive is EDTA-4Na salt;
the initiator used by the anaerobic adhesive is cumene hydroperoxide, benzoyl peroxide and tert-butyl peroxide, preferably cumene hydroperoxide;
the thickening agent used by the anaerobic adhesive can be polyvinyl acetate particles or fumaric acid unsaturated polyester powder and the like.
The preparation method of the anaerobic adhesive comprises the following steps:
(1) the preparation of the anaerobic adhesive needs a planetary stirring kettle, and the reaction temperature in the kettle can be controlled to be 20-50 ℃;
(2) adding a self-made polyurethane acrylic acid oligomer into the kettle, adding a hydroxyl acrylate monoester, an accelerator, an auxiliary accelerator, a polymerization inhibitor and a metal ion chelating agent, heating to 20-30 ℃, continuously stirring until added solid particles are completely dissolved, and uniformly mixing liquid;
(3) adding thickener, etc., heating to 30-50 deg.C, and stirring until solid particles are completely dissolved and uniformly dispersed;
(4) cooling to 20-30 deg.C, adding initiator, stirring until the whole is uniform, and discharging to obtain the anaerobic adhesive.
Compared with the prior art, the invention has the following advantages: the anaerobic adhesive has the advantages of large filling gap, high curing speed, high impact strength and shear strength, excellent water resistance, temperature resistance and medium resistance, can be used for structural bonding, flange plate sealing and the like of various metal materials, and is particularly suitable for flange surface sealing and metal part bonding with high temperature, large vibration and medium corrosion.
Detailed Description
Example one
An anaerobic adhesive is prepared from 91 parts of self-made polyurethane acrylic acid oligomer, 6 parts of hydroxyethyl methacrylate, 0.5 part of acetylphenylhydrazine, 0.5 part of saccharin, 0.03 part of 1, 4-benzoquinone, 0.4 part of EDTA-4Na salt and 1.6 parts of cumene hydroperoxide by mass ratio, and the preparation method comprises the following steps:
firstly, preparing a polyurethane acrylic acid oligomer according to the following steps;
(1) adding 21 parts of isobornyl methacrylate into a closed reaction kettle, adding 9 parts of hydrogenated bisphenol A, heating to 25-30 ℃, and stirring until the mixture is completely dissolved;
(2) adding 15 parts of toluene diisocyanate monomer and 0.05 part of dibutyltin dilaurate, introducing dry nitrogen for protection, heating to the temperature of 45-50 ℃, and carrying out heat preservation reaction for 2.5 h;
(3) adding 40 parts of polytetrahydrofuran diol (molecular weight is 2000), introducing dry nitrogen for protection, heating to 65-70 ℃, and reacting for 2 hours under heat preservation;
(4) adding 15 parts of liquid hydroxypropyl methacrylate, introducing dry nitrogen for protection, and stirring and reacting for 1h at the temperature of 65-70 ℃;
(5) cooling to normal temperature, and discharging to obtain the polyurethane acrylic acid oligomer.
And secondly, preparing the anaerobic adhesive according to the following steps.
(1) Adding 91 parts of the polyurethane acrylic acid oligomer into a planetary kettle, adding 6 parts of hydroxyethyl methacrylate, 0.5 part of acetylphenylhydrazine, 0.5 part of saccharin, 0.03 part of 1, 4-benzoquinone and 0.4 part of EDTA-4Na salt, heating to 20-30 ℃, continuously stirring until solid particles are completely dissolved, and uniformly mixing liquid;
(2) cooling to 20-30 deg.C, adding 1.6 parts of cumene hydroperoxide, stirring, and mixing to obtain the final product.
Example two
An anaerobic adhesive is prepared from 90 parts of self-made polyurethane acrylic acid oligomer, 4 parts of hydroxyethyl methacrylate, 0.8 part of N, N-diethyl-p-toluidine, 0.3 part of saccharin, 0.03 part of 1, 4-benzoquinone, 0.2 part of EDTA-4Na salt and 2 parts of tert-butyl hydroperoxide by mass ratio, and the preparation method comprises the following steps:
firstly, preparing a polyurethane acrylic acid oligomer according to the following steps;
(1) adding 22 parts of isobornyl methacrylate into a closed reaction kettle, adding 10 parts of hydrogenated bisphenol A, heating to 25-30 ℃, and stirring until the mixture is completely dissolved;
(2) adding 16 parts of toluene diisocyanate monomer and 0.05 part of dibutyltin dilaurate, introducing dry nitrogen for protection, heating to the temperature of 45-50 ℃, and carrying out heat preservation reaction for 2.5 h;
(3) adding 43 parts of polytetrahydrofuran diol (molecular weight is 2000), introducing dry nitrogen for protection, heating to 65-70 ℃, and reacting for 2 hours under heat preservation;
(4) adding 20 parts of liquid hydroxypropyl methacrylate, introducing dry nitrogen for protection, and stirring and reacting for 1h at the temperature of 65-70 ℃;
(5) cooling to normal temperature, and discharging to obtain the polyurethane acrylic acid oligomer.
And secondly, preparing the anaerobic adhesive according to the following steps.
(1) Adding 90 parts of the polyurethane acrylic acid oligomer, 4 parts of hydroxyethyl methacrylate, 0.8 part of N, N-diethyl-p-toluidine, 0.3 part of saccharin, 0.03 part of 1, 4-benzoquinone and 0.2 part of EDTA-4Na salt into a planetary kettle, heating to 20-30 ℃, continuously stirring until solid particles are completely dissolved, and uniformly mixing liquid;
(2) cooling to (20-30) ℃, adding 2 parts of tert-butyl hydroperoxide, continuously stirring until the mixture is uniformly mixed, and discharging the glue to obtain the anaerobic glue.
EXAMPLE III
An anaerobic adhesive is prepared from 85 parts of self-made polyurethane acrylic acid oligomer, 8 parts of hydroxyethyl methacrylate, 0.5 part of acetylphenylhydrazine, 0.5 part of saccharin, 0.02 part of 1, 4-benzoquinone, 0.4 part of EDTA-4Na salt, 3 parts of fumaric acid unsaturated polyester powder and 1.6 parts of cumene hydroperoxide by mass ratio, and the preparation method comprises the following steps:
firstly, preparing a polyurethane acrylic acid oligomer according to the following steps;
(1) adding 20 parts of methyl methacrylate into a closed reaction kettle, adding 9 parts of hydrogenated bisphenol A, heating to 25-30 ℃, and stirring until the mixture is completely dissolved;
(2) adding 22 parts of diphenylmethane diisocyanate monomer and 0.05 part of dibutyltin dilaurate, introducing dry nitrogen for protection, heating to the temperature of 45-50 ℃, and carrying out heat preservation reaction for 2 hours;
(3) adding 38 parts of polypropylene glycol (molecular weight is 2000), introducing dry nitrogen for protection, heating to 65-70 ℃, and carrying out heat preservation reaction for 2 hours;
(4) adding 13 parts of liquid hydroxyethyl methacrylate, introducing dry nitrogen for protection, and stirring and reacting for 1h at the temperature of 65-70 ℃;
(5) cooling to normal temperature, and discharging to obtain the polyurethane acrylic acid oligomer.
And secondly, preparing the anaerobic adhesive according to the following steps.
(1) Adding 85 parts of the polyurethane acrylic acid oligomer into a planetary kettle, adding 8 parts of hydroxyethyl methacrylate, 0.5 part of acetylphenylhydrazine, 0.5 part of saccharin, 0.02 part of 1, 4-benzoquinone and 0.4 part of EDTA-4Na salt, heating to 20-30 ℃, continuously stirring until solid particles are completely dissolved, and uniformly mixing liquid;
(2) adding 3 parts of fumaric acid unsaturated polyester powder, heating to 30-50 ℃, continuously stirring until the resin powder is completely dissolved, and uniformly mixing the liquid;
(3) cooling to 20-30 deg.C, adding 1.6 parts of cumene hydroperoxide, stirring, and mixing to obtain the final product.
The test of the relative performance of the anaerobic adhesive of the first embodiment, the second embodiment and the third embodiment is carried out by a standard reference enterprise, wherein the test method of the damp-heat aging resistance strength comprises the following steps: placing the prepared sample piece in an environment with the temperature of 85 ℃ and RH 85% for 168 hours, taking out, cooling to room temperature, and testing the shear strength; determination of storage stability the storage stability was determined as: and (3) injecting 20ml of glue solution into a 50ml polyethylene test tube, placing the test tube into a hot air circulation oven at the temperature of (80 +/-2) DEG C, and observing whether the glue solution is gelled or not after the test tube is placed for 4 hours. The test results are shown in the following table:
the data show that the anaerobic adhesive has high shear strength and impact strength, high curing speed, good storage stability and strength retention rate after moisture-heat aging resistance of more than 80 percent, which indicates that the anaerobic adhesive can meet the requirement of structural bonding, can be rapidly cured when used under the working conditions of severe medium conditions and large vibration, can quickly reach high curing strength and has remarkable advantages compared with other types of anaerobic adhesives.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention, including any reference to the above-mentioned embodiments. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (7)
1. The anaerobic adhesive structural adhesive is characterized by comprising the following components in parts by mass:
70-95 parts of self-made polyurethane acrylic oligomer;
2-10 parts of a hydroxyl acrylate monoester;
0-4 parts of a thickening agent;
0.02-0.20 part of polymerization inhibitor;
0.5-1.5 parts of an accelerator;
0.1-0.5 part of metal ion chelating agent;
0.5-1.5 parts of an auxiliary accelerator;
1.0-3 parts of an initiator;
the self-made polyurethane acrylic oligomer is synthesized by the following raw materials in percentage by mass: 15-25 parts of liquid methacrylate, 5-15 parts of solid bisphenol compounds, 5-25 parts of diisocyanate monomers, 0.02-0.10 part of catalysts, 20-50 parts of polyether diols and 5-20 parts of liquid hydroxyl acrylate monoester compounds; the preparation method comprises the following steps:
(1) the oligomer preparation needs a closed reaction kettle, needs dry nitrogen and ensures that the temperature in the kettle can be accurately controlled;
(2) adding liquid methacrylate into the kettle, then adding the solid bisphenol compound into the liquid methacrylate, heating to 20-30 ℃, and stirring until the solid bisphenol compound is completely dissolved;
(3) adding a diisocyanate monomer and a catalyst, introducing dry nitrogen for protection, heating to 45-55 ℃, and carrying out heat preservation reaction for 1-3 h;
(4) adding polyether glycol, introducing dry nitrogen for protection, heating to 65-75 ℃, and reacting for 1-3 h under heat preservation;
(5) adding a liquid hydroxyl acrylate monoester compound, introducing dry nitrogen for protection, keeping the temperature at 65-75 ℃, and stirring for reaction for 0.5-1.5 hours;
(6) cooling to normal temperature, and discharging to obtain the polyurethane acrylic acid oligomer.
2. An anaerobic adhesive structural adhesive according to claim 1, wherein the solid bisphenol compound selected in the preparation method of the self-made urethane acrylate oligomer is bisphenol a or hydrogenated bisphenol a, the liquid methacrylate is ethyl methacrylate or isobornyl methacrylate, the diisocyanate monomer is toluene diisocyanate or diphenylmethane diisocyanate, the polyether diol is polytetrahydrofuran diol having a molecular weight of 2000 or polypropylene glycol having a molecular weight of 2000, and the liquid hydroxy acrylate monoester is hydroxyethyl methacrylate or hydroxypropyl methacrylate.
3. An anaerobic adhesive structural adhesive according to claim 1, wherein the hydroxy acrylate monoester is hydroxymethyl methacrylate, hydroxyethyl methacrylate or hydroxypropyl methacrylate;
the accelerant is N, N-dimethyl-p-toluidine, N-diethyl-p-toluidine or acetyl phenylhydrazine;
the polymerization inhibitor is 1, 4-naphthoquinone, 1, 4-benzoquinone or hydroquinone;
the auxiliary promoter is saccharin;
the metal ion chelating agent is EDTA-4Na salt;
the initiator is cumyl peroxide, benzoyl peroxide or tert-butyl peroxide;
the thickening agent is polyvinyl acetate particles or fumaric acid unsaturated polyester powder.
4. An anaerobic adhesive structural adhesive according to claim 3, which is prepared from 91 parts by mass of a self-made polyurethane acrylic acid oligomer, 6 parts by mass of hydroxyethyl methacrylate, 0.5 part by mass of acetylphenylhydrazine, 0.5 part by mass of saccharin, 0.03 part by mass of 1, 4-benzoquinone, 0.4 part by mass of EDTA-4Na salt, and 1.6 parts by mass of cumene hydroperoxide.
5. An anaerobic adhesive structural adhesive according to claim 3, which is prepared from 90 parts by mass of self-made polyurethane acrylic acid oligomer, 4 parts by mass of hydroxyethyl methacrylate, 0.8 part by mass of N, N-diethyl-p-toluidine, 0.3 part by mass of saccharin, 0.03 part by mass of 1, 4-benzoquinone, 0.2 part by mass of EDTA-4Na salt and 2 parts by mass of tert-butyl hydroperoxide.
6. An anaerobic adhesive structural adhesive according to claim 3, which is prepared from 85 parts of self-made polyurethane acrylic acid oligomer, 8 parts of hydroxyethyl methacrylate, 0.5 part of acetylphenylhydrazine, 0.5 part of saccharin, 0.02 part of 1, 4-benzoquinone, 0.4 part of EDTA-4Na salt, 3 parts of fumaric acid unsaturated polyester powder and 1.6 parts of cumene hydroperoxide by mass ratio.
7. The method for preparing the anaerobic adhesive structural adhesive according to claim 1, comprising the following steps:
(1) the preparation of the anaerobic adhesive needs a planetary stirring kettle, and the reaction temperature in the kettle can be controlled to be 20-50 ℃;
(2) adding a self-made polyurethane acrylic acid oligomer into the kettle, adding a hydroxyl acrylate monoester, an accelerator, an auxiliary accelerator, a polymerization inhibitor and a metal ion chelating agent, heating to 20-30 ℃, continuously stirring until added solid particles are completely dissolved, and uniformly mixing liquid;
(3) adding thickener, heating to 30-50 deg.C, and stirring until solid particles are completely dissolved and uniformly dispersed;
(4) cooling to 20-30 deg.C, adding initiator, stirring until the whole is uniform, and discharging to obtain the anaerobic adhesive.
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| CN111040720B (en) * | 2019-12-19 | 2021-07-13 | 烟台德邦科技股份有限公司 | Rapid-positioning bi-component polyurethane adhesive and preparation method thereof |
| CN112126386A (en) * | 2020-09-24 | 2020-12-25 | 邵阳把兄弟新材料科技有限公司 | Low-temperature-resistant refrigerating pipeline sealant and preparation method and application thereof |
| CN114716966B (en) * | 2022-05-17 | 2023-07-14 | 烟台信友新材料有限公司 | Flexible anaerobic adhesive suitable for large-clearance curing and used for sealing pipe threads |
| CN117264594A (en) * | 2023-09-12 | 2023-12-22 | 湖南世纪特邦新材料有限公司 | High-pressure-resistant anaerobic adhesive and preparation method and application thereof |
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| CN1057787C (en) * | 1996-11-15 | 2000-10-25 | 北京市天山新材料技术公司 | Anaerobic glue and preparation method |
| CN101824152B (en) * | 2010-04-13 | 2012-05-23 | 深圳职业技术学院 | Preparation method and application of resin having double curing groups |
| CN102079810B (en) * | 2010-12-15 | 2013-03-13 | 北京航空航天大学 | Synthesis and application of light-cured polyurethane-acrylic acid-epoxy resin adhesive |
| CN108329886A (en) * | 2018-03-21 | 2018-07-27 | 烟台泰盛精化科技有限公司 | A kind of resistance to high impact-resistant anaerobic structure glue and preparation method thereof |
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