CN101787239B - Method for preparing environment-friendly powder coating resin - Google Patents
Method for preparing environment-friendly powder coating resin Download PDFInfo
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- CN101787239B CN101787239B CN2009102144938A CN200910214493A CN101787239B CN 101787239 B CN101787239 B CN 101787239B CN 2009102144938 A CN2009102144938 A CN 2009102144938A CN 200910214493 A CN200910214493 A CN 200910214493A CN 101787239 B CN101787239 B CN 101787239B
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- 238000000576 coating method Methods 0.000 title claims abstract description 38
- 239000011248 coating agent Substances 0.000 title claims abstract description 37
- 229920005989 resin Polymers 0.000 title claims abstract description 30
- 239000011347 resin Substances 0.000 title claims abstract description 30
- 239000000843 powder Substances 0.000 title abstract description 21
- 238000000034 method Methods 0.000 title abstract description 15
- 229920001225 polyester resin Polymers 0.000 claims abstract description 24
- 239000004645 polyester resin Substances 0.000 claims abstract description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims description 26
- -1 glycidyl vinyl Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- 150000003504 terephthalic acids Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- 238000006068 polycondensation reaction Methods 0.000 claims description 6
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical class OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 3
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000004925 Acrylic resin Substances 0.000 abstract description 9
- 229920000178 Acrylic resin Polymers 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000001125 extrusion Methods 0.000 abstract 2
- 238000007580 dry-mixing Methods 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 239000002932 luster Substances 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 230000035939 shock Effects 0.000 abstract 1
- 230000008033 biological extinction Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical class OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- Paints Or Removers (AREA)
Abstract
The invention discloses a method for preparing environment-friendly outdoor lusterless powder coating. The method is used for preparing outdoor lusterless powder coating by matching polyester resin with acrylic resin. Without adding a delustering agent or adding a step for dry mixing delustering like double-component powder, the method adopts one-step extrusion and achieves the delustering purpose by directly using the incompatibility of the polyster resin and the acrylic resin and network interpenetrating generated between molecular structures during the curing reaction of the polyster resin and the acrylic resin to achieve accidented microscopic view; and resin A, resin B, an addition agent, pigment and filler are mixed together for melting and extrusion to prepare the outdoor lusterless powder coating with the luster below 10%. The powder coating prepared from carboxyl polyester resin A and glycidyl acrylic resin has good chemical resistance, good weatherability, good powder storage stability and good shock resistance.
Description
Technical field
The present invention relates to be applied to the outdoor glossless powdered coating of environment-friendly type and use performance resins, utilize polyester resin and acrylic resin to arrange in pairs or groups and make the preparation method of outdoor glossless powdered coating.
Background technology
At present; Powder coating is the green coating that a kind of non-volatility organic solvent produces; Because it has characteristics such as resource-saving, solvent-free, low pollutions, coating efficiency height, an application moulding, Application Areas be extensive, and the characteristics that have protection and decorate good combination property, the adaptation coatings industry is to economizing on resources and the energy, alleviating environmental pollution and aspect requirement such as increase work efficiency; Receive global extensive attention, thereby obtain develop rapidly.About 80% has adopted vibrin as main filmogen in the heat curable powder coating market, comprises polyester one epoxy mixed powder coating, weatherable polyether powder coating etc.Lot of documents has been reported with polyvalent alcohol and the polyprotonic acid/acid method of direct esterification synthesizing polyester resin that fitted over catalyst action, but many methods make the poor-performings such as weathering resistance of powder coating; And all can't accomplish glossless powdered coating with resin making outdoor extinction powder material.Present outdoor extinction powder coating mainly is to realize through physics delustring, chemical quenching, the delustring of two component dry blending.And the prepared extinction powder coating gloss of these extinction methods is difficult to accomplish that all more than 10% gloss is at the outdoor glossless powdered coating below 10%.
Summary of the invention
The objective of the invention is to overcome above-mentioned deficiency, provide and utilize polyester resin and acrylic resin to arrange in pairs or groups to make the preparation method of outdoor glossless powdered coating.Good, the leveling characteristics excellent property of outdoor glossless powdered coating resin material good weatherability, chemicals-resistant of this method preparation.
The present invention realizes above-mentioned purpose through following technical scheme:
The preparation method of the outdoor glossless powdered coating of a kind of environment-friendly type is characterized in that it is to be prepared from terminal carboxyl polyester resin A and glycidyl vinyl resin B, auxiliary agent and color stuffing, and its terminal carboxyl polyester resin A prepares through following steps:
(1), in polycondensation vessel, drop into polyvalent alcohol, its feed composition weight ratio: NSC 6366 (NPG) is 60 parts, 20 parts of 1,4 cyclohexanedimethanols (CHDM), 2 parts of tetramethylolmethanes (PNT), 15 parts of pinakons (HDG); Be warming up to 120 ℃;
(2), the weighing polyprotonic acid, its feed composition weight ratio: 80 parts of terephthalic acids (TPA), 8 parts of m-phthalic acids (IPA), 8 parts of hexanodioic acids (ADA), 8 parts of HHPAs (HHPAA); 95～98% of total amount is wherein dropped in the stills, stay 2%～5% in subsequent handling acid adjustment subsequent use;
(3), the polycondensation vessel temperature is transferred to 200～240 ℃, reacted 10～15 hours;
(4), survey acid number and reach 10mgkoH/g, mend and throw 2%～5% remaining in (2) step polyprotonic acid, react to acid number 30mgkoH/g, be cooled to 100～150 ℃, form Resin A;
Its glycidyl vinyl resin B prepares through following steps:
(1), is warming up to 85 ℃～95 ℃ by weight in reaction kettle, adding 13 parts of Virahols;
(2), with after 10～20 parts of propenoate that comprise ethyl propenoate, methyl acrylate, TEB 3K, Isooctyl acrylate monomer and 0.6 part of dissolving of initiator Diisopropyl azodicarboxylate with 3 parts of glycidyl acrylate mixings, epoxy equivalent (weight) is controlled at 500～600;
(3) mixture slowly is added dropwise in the reaction kettle, strict controlled temperature is incubated 2 hours at 85 ℃～95 ℃, vacuumizes the separation solvent and obtains resin B;
On the basis of the above, terminal carboxyl polyester resin A and glycidyl vinyl resin B, auxiliary agent, color stuffing are mixed together evenly, it is following specifically to add the quantity weight part:
With twin screw extruder melt extrude, compressing tablet, first broken thick sheet stock;
Then, the thick sheet stock of last gained is dropped into kibbler ground 200 mesh sieves, obtain grain through less than 80 microns gloss in the open air of the environment-friendly type 10% below glossless powdered coating.
As further specifying of such scheme; In the preparation process of said glycidyl vinyl resin B, the component weight ratio of the said propenoate that (2) step gathered is 1 part of ethyl propenoate, 3 parts of methyl acrylates, 8 parts of TEB 3Ks, 1 part of Isooctyl acrylate monomer.
Method of the present invention need not to add in addition matting agent, also need not to come the dry blending delustring as the many one procedure of two-pack powder; But the disposable immiscible property of directly utilizing polyester resin and acrylic resin and polyester resin and acrylic resin extruded produces network interpenetrating between the molecular structure and makes and the uneven purpose that reaches delustring of microcosmic of filming can obtain gloss at the outdoor glossless powdered coating below 10% when curing reaction; The powder coating that its terminal carboxyl polyester resin A and glycidyl vinyl resin B process has good chemical-resistant, good weather, good powder stability in storage and shock-resistance; Resin A and resin B, auxiliary agent, color stuffing are mixed together disposable melt and dissolved the extruding in back can make gloss at the outdoor glossless powdered coating below 10%.
Embodiment:
The outdoor glossless powdered coating resin of environment-friendly type of the present invention, it is mainly formed and comprises terminal carboxyl polyester resin A and glycidyl vinyl resin B.Wherein terminal carboxyl polyester resin A be it mainly by polynary it be mainly to constitute by polyvalent alcohol, polyprotonic acid; The material component weight ratio is for for polyvalent alcohol: (NPG is 60 parts, 20 parts of 1,4 cyclohexanedimethanols (CHDM), 2 parts of tetramethylolmethanes (PNT), 15 parts of pinakons (HDG) to NSC 6366; Polyprotonic acid: 80 parts of terephthalic acids (TPA), 8 parts of m-phthalic acids (IPA), 8 parts of hexanodioic acids (ADA), 8 parts of HHPAs (HHPAA).Its material component of glycidyl vinyl resin B and weight ratio are: 13 parts of Virahols, 1 part of ethyl propenoate, 3 parts of methyl acrylates, 8 parts of TEB 3Ks, 1 part of the different monooctyl ester of olefin(e) acid, 3 parts of glycidyl acrylates, 0.6 part of initiator Diisopropyl azodicarboxylate.
The preparation method of above-mentioned powder coating resin, its terminal carboxyl polyester resin A step comprises:
(1) in polycondensation vessel, drops into polyvalent alcohol, 60 parts of the NSC 6366s of getting the raw materials ready (NPG), 20 parts of 1,4 cyclohexane dimethanols (CHDM), 2 parts of tetramethylolmethanes (PNT), 15 parts of pinakons (HDG), elevated temperature to 120 ℃;
(2) weighing polyprotonic acid, 80 parts of terephthalic acids (TPA), 8 parts of m-phthalic acids (IPA), 8 parts of hexanodioic acids (ADA), 8 parts of HHPAs (HHPAA), will be wherein 95～98% polyprotonic acids drop in the still, stay 2%～5% in subsequent handling acid adjustment subsequent use;
(3) the polycondensation vessel temperature is transferred to 240 ℃, reacted 15 hours;
(4) survey acid number and reach 10mgkoH/g, mend and throw remaining 2%～5% polyprotonic acid, react, be cooled to 100～150 ℃, form Resin A to acid number 30mgkoH/g.
The synthesis technique of vinyl resin is following:
In reaction kettle, added Virahol 13 minutes; Be warming up to 85 ℃～95 ℃; With 1 part of ethyl propenoate, 3 parts of methyl acrylates, 8 parts of TEB 3Ks, 1 part and 0.6 part initiator dissolving of Isooctyl acrylate monomer back and 3 parts of glycidyl acrylate mixings, this moment, epoxy equivalent (weight) was controlled at 500～600, slowly was added dropwise to said mixture in the reaction kettle; Strict controlled temperature slowly drips said mixture and in 4 hours, dropwises at 85 ℃～95 ℃.Be incubated 2 hours, vacuumize desolventizing and obtain resin B.
Above-mentioned discharging product, through the main performance index such as the following table of sampling inspection:
| Sequence number | Project | Unit | Carboxyl polyester resin | The glycidyl vinyl resin |
| 1 | Outward appearance | ---- | White is to faint yellow | The white transparent grain |
| 2 | Viscosity (160 ℃) | CP | 80～180 | 200-280 |
| 3 | Acid number | mgkoH/g | 45～60 | ---- |
| 4 | Epoxy equivalent (weight) | EEW | ---- | 500-600 |
| 5 | Second-order transition temperature | ℃ | 50～60 | 58-65 |
| 6 | Softening temperature | ℃ | 90～105 | 105-110 |
| 7 | Non-volatile content | ％ | 100 | 100 |
The outdoor glossless powdered coating of the inventive method synthetic environment-friendly type is used resin, can embody through the performance of utilizing polyester resin and acrylic resin to arrange in pairs or groups to make outdoor glossless powdered coating.Their reactive chemistry tries as follows:
As shown in table 1, manufacturing step: after being mixed together terminal carboxyl polyester resin A and glycidyl vinyl resin B, auxiliary agent, color stuffing evenly, with twin screw extruder melt extrude, compressing tablet, first broken thick sheet stock.The thick sheet stock of gained is dropped into kibbler ground 200 mesh sieves, obtain grain through less than 80 microns gloss in the open air of the environment-friendly type 10% below glossless powdered coating.Powder coating adopts electrostatic spraying on metal sheet, and film thickness monitoring is between the 50-120 micron, and through 200 ℃ of X10～15 minute baking-curing film forming, film performance that obtains such as following table 1 are listed.
Experimental data shows, adopts the composition of formulation weight part of the present invention can obtain best effect, and as in the process of preparation terminal carboxyl polyester resin A, when elevated temperature surpassed 120 ℃, then its resin was prone to flavescence; Technical formula with respect to outside other the present invention prescription is compared, and the powder coating that its terminal carboxyl polyester resin A and glycidyl vinyl resin B process has good chemical-resistant, good weather, good powder stability in storage and shock-resistance; Resin A and resin B, auxiliary agent, color stuffing are mixed together disposable melt and dissolved the extruding in back can make gloss, have good application effect at the outdoor glossless powdered coating below 10%.
Claims (2)
1. the preparation method of the outdoor glossless powdered coating of environment-friendly type is characterized in that it is to be prepared from terminal carboxyl polyester resin A and glycidyl vinyl resin B, auxiliary agent and color stuffing, and its terminal carboxyl polyester resin A prepares through following steps:
(1), in polycondensation vessel, drop into polyvalent alcohol, its feed composition weight ratio: NSC 6366 is 60 parts, 20 parts of 1,4 cyclohexanedimethanols, 2 parts of tetramethylolmethanes, 15 parts of pinakons; Be warming up to 120 ℃;
(2), the weighing polyprotonic acid, its feed composition weight ratio: 80 parts of terephthalic acids, 8 parts of m-phthalic acids, 8 parts of hexanodioic acids, 8 parts of HHPAs; 95～98% of total amount is wherein dropped in the stills, stay 2%～5% in subsequent handling acid adjustment subsequent use;
(3), the polycondensation vessel temperature is transferred to 200～240 ℃, reacted 10～15 hours;
(4), survey acid number and reach 10mgkoH/g, mend and throw 2%～5% remaining in (2) step polyprotonic acid, react to acid number 30mgkoH/g, be cooled to 100～150 ℃, form Resin A;
Its glycidyl vinyl resin B prepares through following steps:
(1), is warming up to 85 ℃～95 ℃ by weight in reaction kettle, adding 13 parts of Virahols;
(2), with after 10～20 parts of propenoate that comprise ethyl propenoate, methyl acrylate, TEB 3K, Isooctyl acrylate monomer and 0.6 part of dissolving of initiator Diisopropyl azodicarboxylate with 3 parts of glycidyl acrylate mixings, epoxy equivalent (weight) is controlled at 500～600;
(3) mixture slowly is added dropwise in the reaction kettle, strict controlled temperature is incubated 2 hours at 85 ℃～95 ℃, vacuumizes the separation solvent and obtains resin B;
On the basis of the above, terminal carboxyl polyester resin A and glycidyl vinyl resin B, auxiliary agent, color stuffing are mixed together evenly, it is following specifically to add the quantity weight part:
With twin screw extruder melt extrude, compressing tablet, first broken thick sheet stock;
Then, the thick sheet stock of last gained is dropped into kibbler ground 200 mesh sieves, obtain grain through less than 80 microns gloss in the open air of the environment-friendly type 10% below glossless powdered coating.
2. the preparation method of the outdoor glossless powdered coating of environment-friendly type according to claim 1; It is characterized in that; In the preparation process of said glycidyl vinyl resin B, the component weight ratio of the said propenoate that (2) step gathered is 1 part of ethyl propenoate, 3 parts of methyl acrylates, 8 parts of TEB 3Ks, 1 part of Isooctyl acrylate monomer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102144938A CN101787239B (en) | 2009-12-31 | 2009-12-31 | Method for preparing environment-friendly powder coating resin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102144938A CN101787239B (en) | 2009-12-31 | 2009-12-31 | Method for preparing environment-friendly powder coating resin |
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| CN101787239A CN101787239A (en) | 2010-07-28 |
| CN101787239B true CN101787239B (en) | 2012-05-23 |
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| CN104119783A (en) * | 2014-06-27 | 2014-10-29 | 南京屏湖粉末材料有限公司 | Weather-resistant powder coating |
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| CN117925032A (en) * | 2022-05-06 | 2024-04-26 | 东胜化学(上海)有限公司 | Paint with good extinction property and production method thereof |
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Address after: 528100 fan Lake Economic Development Zone, Leping Town, Sanshui District, Guangdong, Foshan Patentee after: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Address before: 528100 fan Lake Economic Development Zone, Leping Town, Sanshui District, Guangdong, Foshan Patentee before: GUANGDONG YINYANG RESIN Co.,Ltd. |
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Denomination of invention: Method for preparing environment-friendly powder coating resin Effective date of registration: 20171117 Granted publication date: 20120523 Pledgee: Guangzhou master Asset Management Co.,Ltd. Pledgor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Registration number: 2017440000138 |
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Denomination of invention: Method for preparing environment-friendly powder coating resin Effective date of registration: 20180706 Granted publication date: 20120523 Pledgee: Guangzhou master Asset Management Co.,Ltd. Pledgor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Registration number: 2018440000190 |
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Denomination of invention: Preparation method of environment friendly outdoor matte powder coatings Effective date of registration: 20210508 Granted publication date: 20120523 Pledgee: Guangdong Yaoda Financial Leasing Co.,Ltd. Pledgor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Registration number: Y2021980003370 |
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