CN115505112A - Low-cost and low-gloss polyester resin for powder coating and preparation method thereof - Google Patents
Low-cost and low-gloss polyester resin for powder coating and preparation method thereof Download PDFInfo
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- CN115505112A CN115505112A CN202211320120.0A CN202211320120A CN115505112A CN 115505112 A CN115505112 A CN 115505112A CN 202211320120 A CN202211320120 A CN 202211320120A CN 115505112 A CN115505112 A CN 115505112A
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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
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
Abstract
The invention relates to a low-cost and low-gloss polyester resin for powder coating, which is mainly obtained by polymerizing hydrolyzed polymaleic anhydride aqueous solution, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid and hydroxyl polyester resin. On the basis of no need of adding a flatting agent, the prepared powder coating has obvious carboxyl difference and hydroxyl difference, the final coating film of the powder coating after curing can stably realize 10-18% of flatting effect, the surface fineness is good, other properties can also meet the application requirements, and the cost is low without using complex raw materials and processes.
Description
Technical Field
The invention relates to the field of powder coatings, in particular to a low-cost and low-gloss polyester resin for a powder coating and a preparation method thereof.
Background
The powder paint is a solid powder synthetic resin paint composed of solid resin, pigment, filler and assistant. Unlike common solvent-based coatings and water-based coatings, the dispersion medium is not a solvent and water, but air. It has the features of no solvent pollution, 100% filming and low power consumption, and has excellent performance and thus wide application.
The HAA curing agent is named as N, N, N ', N' -tetra (2-hydroxyethyl) adipamide (CAS number is 6334-25-4), has the advantages of low cost, no irritation and the like, and the prepared HAA system powder coating has low cost and small dosage, so the finished powder coating of the HAA curing system has low cost, and the application amount of the finished powder coating is rapidly expanded. In recent years, as the price of the E-12 epoxy resin used as the raw material of indoor powder coatings increases, HAA system powder coatings have excellent cost advantages and are increasingly used for coating indoor furniture from the original outdoor coating.
However, although the HAA system powder coating has excellent overall properties and low cost, it has a significant drawback that the curing speed is too uniform to be matt due to the small difference in activity of the four hydroxyl groups of HAA, and it is difficult to obtain a coating film for low gloss decoration in most cases, a coating film having a gloss of 90% or more is obtained.
In order to solve the problem, related companies also research a matting agent for the HAA system, such as a matting agent product prepared by matching wax powder and an emulsifier in CN201910838549.0, but the gloss can be reduced to 20-30%, and increasing the dosage can not only effectively reduce the gloss, but also bring about the defect of film coating and the surface blurring caused by excessive wax powder. CN202010668166.6 needs more kinds of additives in the process of preparing powder coating, and two carboxyl polyesters are used simultaneously, wherein one polyester resin is a polyester resin with high acid value, which is actually equivalent to dry mixing extinction, and the stability of the preparation process is poor. While CN201810753591.8 can achieve extinction of 10-20%, since part of raw materials contain a large amount of functional groups, the cost of the raw materials is relatively high, and it is difficult for downstream customers to use the raw materials on a large scale.
Disclosure of Invention
Aiming at the problem that the extinction is poor when the conventional HAA system powder coating is applied to the direction of indoor decorative powder coatings on the basis of having the cost advantage, the scheme is designed by starting from molecular structure connection, and adopts low-cost carboxyl-intensive polymaleic anhydride and specially-selected hydroxyl polyester resin for reaction, so that the powder coating prepared from the finally-obtained polyester resin has obvious differences in the positions, the activities and the steric hindrance of carboxyl, and the hydroxyl in the system has the hydroxyl of a hydroxyl polyester chain segment and the hydroxyl in an HAA curing agent, therefore, the prepared powder coating has obvious carboxyl difference and hydroxyl difference on the basis of not needing an external flatting agent, a coating film obtained after the powder coating is cured can stably achieve 10-18% of extinction effect, the surface fineness is good, other properties can meet the application requirements, complex raw materials and processes are not needed, and the cost is low.
The invention relates to a low-cost and low-gloss polyester resin for powder coating, which is obtained by polymerizing hydrolyzed polymaleic anhydride aqueous solution, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid and hydroxyl polyester resin.
A low cost, low gloss polyester resin for powder coatings such as those described above, hydrolyzed polymaleic anhydride aqueous solution, HPMA, having a solids content of 55%, is available from, for example, shandong Tai and Water treatment technologies, inc.; the hydroxyl value of the hydroxyl polyester resin is 38-43mgKOH/g, and the glass transition temperature Tg is 62-65 ℃; for example, model number may be SJ1100, available from new materials of swords, inc.
The polyester resin for the low-cost and low-gloss powder coating comprises the following raw materials in parts by weight:
25-50 parts of hydrolyzed polymaleic anhydride aqueous solution;
16-25 parts of terephthalic acid;
15-30 parts of neopentyl glycol;
5-10 parts of diethylene glycol;
8-18 parts of isophthalic acid;
6-12 parts of hydroxyl polyester resin;
the raw material also comprises a certain amount of catalyst and antioxidant.
The dosage of the catalyst is 0.1 to 0.2 percent of the total mass of the main raw materials; the catalyst is preferably monobutyltin oxide.
The dosage of the antioxidant is 0.1-0.2% of the total mass of the main raw materials; the antioxidant is preferably 1010, i.e., tetrakis [ methyl-beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] pentaerythritol ester.
The invention also relates to a preparation method of the polyester resin, which comprises the following steps:
A. adding the hydrolytic polymaleic anhydride aqueous solution with the formula ratio into an overhead tank for later use;
B. adding terephthalic acid, neopentyl glycol, diethylene glycol and a catalyst according to the formula ratio into a reaction kettle, heating to 130-135 ℃, fully stirring uniformly, heating and preserving heat to perform polycondensation reaction;
C. sampling and detecting, when the acid value of the polymer is 80-90mgKOH/g, beginning to dropwise add the hydrolytic polymaleic anhydride aqueous solution in a high-temperature groove, dropwise adding 1/3 of the formula amount, completing dropwise adding within 1h, gradually heating after completing dropwise adding, and continuing to perform heat preservation polymerization reaction;
D. when the acid value of the polymer reaches 15-22mgKOH/g, adding the isophthalic acid with the formula amount, simultaneously dropwise adding the rest of the hydrolytic polymaleic anhydride aqueous solution, finishing dropwise adding within 1h, and then continuing to perform heat preservation polymerization reaction;
E. sampling and detecting, adding antioxidant with formula amount when the acid value in the polymer reaches 60-70mgKOH/g, starting a vacuum system, and heating to 230-235 ℃ to perform vacuum polycondensation reaction again;
E. when the acid value of the polymer reaches 50-55mgKOH/g, releasing the vacuum, adding the hydroxyl polyester resin with the formula amount, stirring at 230-235 ℃, melting, mixing and reacting;
F. stopping the reaction when the acid value of the polymer reaches 38-43mgKOH/g and the hydroxyl value is 8-15mgKOH/g, discharging at high temperature, cooling the polyester resin, and then crushing and granulating to obtain the polyester resin.
Further, in the step B, heating to 175-180 ℃ at a heating rate of 12-15 ℃/h, and carrying out a polycondensation reaction under heat preservation; in the step C, gradually heating to 220-230 ℃ at the heating speed of 8-10 ℃; controlling the vacuum degree of the vacuum system in the step E to be-0.095 Mpa to-0.097 Mpa; and F, cooling the polyester resin by using a steel belt with condensed water.
The invention also relates to the application of the polyester resin for the low-cost and low-gloss powder coating or the polyester resin obtained by the method in a HAA curing system.
The obtained product is colorless transparent particles, and has an acid value of 38-43mgKOH/g, a hydroxyl value of 8-15mgKOH/g and a softening point of 115-127 ℃.
The invention has the beneficial effects that:
the low-cost and low-gloss polyester resin for the powder coating is mainly obtained by polymerizing hydrolyzed polymaleic anhydride aqueous solution, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid and hydroxyl polyester resin. The polyester resin simultaneously contains carboxyl polyester resin and hydroxyl polyester resin, wherein a carboxyl group of segmented polymaleic anhydride and a carboxyl group of isophthalic acid are formed in a carboxyl polyester structure, and the carboxyl groups of polymaleic anhydride are dense and have large steric hindrance.
Detailed Description
In order to facilitate an understanding of the invention, various exemplary embodiments of the invention will now be described in detail, which should not be construed as a specific limitation of the invention, but rather as a more detailed description of certain aspects, features and embodiments of the invention.
In the raw materials, the hydrolytic polymaleic anhydride aqueous solution, namely HPMA, has the solid content of 55 percent and is purchased from Shandongtai and Water treatment science and technology Co., ltd; the hydroxyl polyester resin is SJ1100, and is purchased from New Material Ltd of Anhui Shenjian; the rest are all common commercial products.
Example 1
The polyester resin raw material for the powder coating comprises the following components in parts by mass:
27 parts of hydrolytic polymaleic anhydride aqueous solution;
18 parts of terephthalic acid;
neopentyl glycol 16 parts;
6 parts of diethylene glycol;
8 parts of isophthalic acid;
7 parts of hydroxyl polyester resin;
the catalyst is monobutyl tin oxide, and the using amount of the monobutyl tin oxide is 0.1 percent of the total mass of the main raw materials;
the antioxidant is 1010, namely tetra [ methyl-beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] pentaerythritol ester, and the using amount of the antioxidant is 0.2 percent of the total mass of the main raw materials;
the preparation method comprises the following steps:
A. adding the hydrolytic polymaleic anhydride aqueous solution with the formula ratio into an overhead tank for later use;
B. adding terephthalic acid, neopentyl glycol, diethylene glycol and a catalyst according to the formula ratio into a reaction kettle, heating to 132 ℃, fully stirring uniformly, heating to 180 ℃ at a heating rate of 13 ℃/h, and carrying out heat preservation polycondensation reaction;
C. sampling and detecting, when the acid value of the polymer is 85mgKOH/g, beginning to dropwise add the hydrolytic polymaleic anhydride aqueous solution in a high-temperature groove, dropwise adding 1/3 of the formula amount, completing dropwise adding within 1h, gradually heating to 230 ℃ at the heating rate of 10 ℃ after completing dropwise adding, and then continuing to perform heat preservation polymerization reaction;
D. when the acid value of the polymer reaches 20mgKOH/g, adding isophthalic acid with the formula amount, simultaneously dropwise adding the rest of the aqueous solution of the hydrolyzed polymaleic anhydride, finishing dropwise adding within 1h, and then continuing the heat-preservation polymerization reaction;
E. sampling and detecting, adding antioxidant with formula amount when the acid value in the polymer reaches 65mgKOH/g, then starting a vacuum system, controlling the vacuum degree at-0.096 Mpa, and heating to 233 ℃ for vacuum polycondensation again;
E. when the acid value of the polymer reaches 52mgKOH/g, the vacuum is relieved, hydroxyl polyester resin with the formula amount is added, and the mixture is stirred, melted, mixed and reacted at 232 ℃;
F. and when the acid value and the hydroxyl value of the polymer reach the following targets, stopping the reaction, discharging at high temperature while the polymer is hot, cooling the polyester resin by using a steel belt with condensed water, and crushing and granulating to obtain the polyester resin.
Finally, the prepared polyester resin has an acid value of 40mgKOH/g, a hydroxyl value of 15mgKOH/g and a softening point of 116 ℃.
Example 2
The polyester resin for the powder coating comprises the following raw materials in parts by mass:
48 parts of hydrolytic polymaleic anhydride aqueous solution;
24 parts of terephthalic acid;
neopentyl glycol 28 parts;
8 parts of diethylene glycol;
16 parts of isophthalic acid;
10 parts of hydroxyl polyester resin;
the catalyst is monobutyl tin oxide, and the using amount of the catalyst is 0.1 percent of the total mass of the main raw materials;
the antioxidant is antioxidant 1010, and the dosage of the antioxidant is 0.1 percent of the total mass of the main raw materials;
the preparation method is the same as example 1.
Finally, the prepared polyester resin has an acid value of 42mgKOH/g, a hydroxyl value of 13mgKOH/g and a softening point of 125 ℃.
Example 3
The polyester resin raw material for the powder coating comprises the following components in parts by mass:
38 parts of hydrolytic polymaleic anhydride aqueous solution;
20 parts of terephthalic acid;
23 parts of neopentyl glycol;
7 parts of diethylene glycol;
14 parts of isophthalic acid;
10 parts of hydroxyl polyester resin;
the catalyst is monobutyl tin oxide, and the using amount of the catalyst is 0.2 percent of the total mass of the main raw materials;
the antioxidant is antioxidant 1010, and the using amount of the antioxidant is 0.2 percent of the total mass of the main raw materials;
the preparation method is the same as example 1.
Finally, the prepared polyester resin has an acid value of 39mgKOH/g, a hydroxyl value of 12mgKOH/g and a softening point of 120 ℃.
Example 4
The polyester resin raw material for the powder coating comprises the following components in parts by mass:
42 parts of hydrolytic polymaleic anhydride aqueous solution;
18 parts of terephthalic acid;
neopentyl glycol 26 parts;
8 parts of diethylene glycol;
12 parts of isophthalic acid;
9 parts of hydroxyl polyester resin;
the catalyst is monobutyl tin oxide, and the dosage of the monobutyl tin oxide is 0.2 percent of the total mass of the main raw materials;
the antioxidant is antioxidant 1010, and the using amount of the antioxidant is 0.2 percent of the total mass of the main raw materials;
the preparation method is the same as example 1.
Finally, the prepared polyester resin has an acid value of 40mgKOH/g, a hydroxyl value of 10mgKOH/g and a softening point of 122 ℃.
Comparative example 1: commercially available HAA polyester resin (acid value: 33mgKOH/g, hydroxyl value: 0.8mgKOH/g, softening point 112 ℃ C., model ZJ9505, huangshan Zhengjie New Material Co., ltd.).
Application example
The conventional powder coating formula is adopted and is usually as follows in parts by weight:
preparing a coating layer: and uniformly mixing the materials according to the formula of the normal HAA system powder coating, extruding, tabletting and crushing by using a double-screw extruder, and then crushing and sieving the tablets to prepare the powder coating. And spraying the powder coating on the galvanized iron substrate subjected to surface treatment by using an electrostatic spray gun, and curing at 180 ℃/20min to obtain the coating.
The detection basis of the coating indexes is as follows: GB/T21776-2008 Standard guidelines for testing powder coatings and coatings therefor. The gloss of the coating film is tested by adopting an angle of 60 degrees; the leveling grade is carried out by adopting a PCI (peripheral component interconnect) grading method, the level is 0-10, and the higher the number is, the better the leveling is.
TABLE 1 coating film Properties of examples and comparative examples
As can be seen from the table 1, the product prepared by the scheme of the invention can achieve the gloss of 10-15% without adding a flatting agent, the difference of the types, positions and activities of carboxyl groups in polyester chain segments is fully utilized, the difference of the curing speed and the flatting are finally achieved by means of the difference of the types and activities of hydroxyl groups, the curing time needs to be prolonged to 20min to achieve the effects of full curing and high leveling, the cost of the selected raw materials of the product is low, the single polyester resin is prepared under a special process, the application is convenient, and the prepared powder coating has good stability.
Comparative example 1 used a conventional commercially available HAA-system polyester resin, and its gloss was over 90% without adding a matting agent, and it was difficult to obtain a low-gloss powder coating excellent in decorativeness.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the spirit or scope of the invention.
Claims (10)
1. The polyester resin for the low-cost and low-gloss powder coating is characterized in that the raw materials comprise hydrolyzed polymaleic anhydride aqueous solution, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid and hydroxyl polyester resin, and the polyester resin is obtained by polymerization of the hydrolyzed polymaleic anhydride aqueous solution, the terephthalic acid, the neopentyl glycol, the diethylene glycol, the isophthalic acid and the hydroxyl polyester resin.
2. The low cost, low gloss polyester resin of claim 1 wherein the hydrolyzed polymaleic anhydride aqueous solution has a solids content of 55%; the hydroxyl value of the hydroxyl polyester resin is 38-43mgKOH/g, and the glass transition temperature Tg is 62-65 ℃.
3. The low-cost and low-gloss polyester resin for powder coatings according to claim 1 or 2, wherein the polyester resin raw materials comprise the following components in parts by weight:
25-50 parts of hydrolyzed polymaleic anhydride aqueous solution;
16-25 parts of terephthalic acid;
15-30 parts of neopentyl glycol;
5-10 parts of diethylene glycol;
8-18 parts of isophthalic acid;
6-12 parts of hydroxyl polyester resin;
the raw materials also comprise a certain amount of catalyst and antioxidant.
4. The low-cost and low-gloss polyester resin for powder coatings according to claim 3, characterized in that the components further comprise a catalyst in an amount of 0.1 to 0.2% of the total mass of the main raw materials; the catalyst is preferably monobutyltin oxide.
5. The low-cost and low-gloss polyester resin for powder coatings as claimed in claim 3, wherein the components further comprise an antioxidant in an amount of 0.1 to 0.2 percent of the total mass of the main raw materials; the antioxidant is preferably antioxidant 1010.
6. A method for preparing the polyester resin according to any one of claims 1 to 5, comprising the steps of:
A. adding the hydrolytic polymaleic anhydride aqueous solution with the formula ratio into an overhead tank for later use;
B. adding terephthalic acid, neopentyl glycol, diethylene glycol and a catalyst in a formula ratio into a reaction kettle, heating to 130-135 ℃, fully stirring uniformly, heating and preserving heat to perform polycondensation reaction;
C. sampling and detecting, when the acid value of the polymer is 80-90mgKOH/g, beginning to dropwise add the hydrolytic polymaleic anhydride aqueous solution in a high-temperature groove, dropwise adding 1/3 of the formula amount, completing dropwise adding within 1h, gradually heating after completing dropwise adding, and continuing to perform heat preservation polymerization reaction;
D. adding isophthalic acid with the formula amount when the acid value of the polymer reaches 15-22mgKOH/g, simultaneously dropwise adding the rest of the aqueous solution of the hydrolyzed polymaleic anhydride within 1h, and then continuing the heat-preservation polymerization reaction;
E. sampling and detecting, adding the antioxidant with the formula amount when the acid value in the polymer reaches 60-70mgKOH/g, starting a vacuum system, and heating to 230-235 ℃ to perform vacuum polycondensation again;
E. when the acid value of the polymer reaches 50-55mgKOH/g, releasing the vacuum, adding the hydroxyl polyester resin with the formula amount, stirring at 230-235 ℃, melting, mixing and reacting;
F. stopping the reaction when the acid value of the polymer reaches 38-43mgKOH/g and the hydroxyl value reaches 8-15mgKOH/g, discharging at high temperature, cooling the polyester resin, and crushing and granulating to obtain the polyester resin.
7. The method for preparing polyester resin according to claim 6, wherein in the step B, the polycondensation reaction is performed by raising the temperature to 175-180 ℃ at a temperature raising rate of 12-15 ℃/h and maintaining the temperature.
8. The process for producing polyester resin according to claim 6, wherein in the step C, the temperature is gradually increased to 220-230 ℃ at a temperature increasing rate of 8-10 ℃.
9. The method for preparing polyester resin according to claim 6, wherein the degree of vacuum of the vacuum system in the step E is controlled to be-0.095 Mpa to-0.097 Mpa; and F, cooling the polyester resin by using a steel belt with condensed water.
10. Use of a low cost, low gloss powder coating polyester resin according to claims 1-5 or obtained by the process according to claims 6-9 in HAA curing systems.
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| CN202211320120.0A CN115505112B (en) | 2022-10-26 | 2022-10-26 | Low-cost low-light type polyester resin for powder coating and preparation method thereof |
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| CN202211320120.0A CN115505112B (en) | 2022-10-26 | 2022-10-26 | Low-cost low-light type polyester resin for powder coating and preparation method thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501667A (en) * | 1983-03-03 | 1985-02-26 | Ciba-Geigy Corporation | Process of inhibiting corrosion of metal surfaces and/or deposition of scale thereon |
| CA2131745A1 (en) * | 1994-09-09 | 1996-03-10 | Takafumi Umehara | Low Gloss Powder Coating Composition and Method for Coating Therewith |
| CN110483751A (en) * | 2018-07-10 | 2019-11-22 | 黄山学院 | A kind of HAA system extinction type polyester resin and the preparation method and application thereof |
| CN113201126A (en) * | 2021-05-27 | 2021-08-03 | 黄山佳杰新材料科技有限公司 | Semi-crystalline polyester resin and powder coating |
-
2022
- 2022-10-26 CN CN202211320120.0A patent/CN115505112B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501667A (en) * | 1983-03-03 | 1985-02-26 | Ciba-Geigy Corporation | Process of inhibiting corrosion of metal surfaces and/or deposition of scale thereon |
| CA2131745A1 (en) * | 1994-09-09 | 1996-03-10 | Takafumi Umehara | Low Gloss Powder Coating Composition and Method for Coating Therewith |
| CN110483751A (en) * | 2018-07-10 | 2019-11-22 | 黄山学院 | A kind of HAA system extinction type polyester resin and the preparation method and application thereof |
| CN113201126A (en) * | 2021-05-27 | 2021-08-03 | 黄山佳杰新材料科技有限公司 | Semi-crystalline polyester resin and powder coating |
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