CN115505112B - Low-cost low-light type polyester resin for powder coating and preparation method thereof - Google Patents
Low-cost low-light type polyester resin for powder coating and preparation method thereof Download PDFInfo
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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
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- Polyesters Or Polycarbonates (AREA)
Abstract
The present invention relates to a low-cost, low-gloss polyester resin for powder coating, which is mainly obtained by polymerizing a hydrolyzed aqueous maleic anhydride solution, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid, and a hydroxyl polyester resin. On the basis of no need of adding an flatting agent, obvious carboxyl difference and hydroxyl difference exist in the prepared powder coating, and finally, the coating film after the powder coating is solidified can stably realize 10-18% flatting effect, the surface fineness is better, other performances can meet the application requirements, and complex raw materials and processes are not needed, so that the cost is lower.
Description
Technical Field
The invention relates to the field of powder coatings, in particular to a low-cost and low-light type polyester resin for a powder coating and a preparation method thereof.
Background
The powder coating is a solid powder synthetic resin coating composed of solid resin, pigment, filler, auxiliary agent and the like. Unlike common solvent-based paint and water-based paint, its dispersion medium is not solvent and water, but air. The film has the characteristics of no solvent pollution, 100% film formation and low energy consumption, and is widely applied due to the very excellent performance.
The HAA curing agent has the chemical name of N, N, N ', N' -tetra (2-hydroxyethyl) adipamide (CAS number 6334-25-4) and has the advantages of low cost, no irritation and the like, and the prepared HAA system powder coating has low cost and small dosage of the HAA curing agent, so that the cost of the finished powder coating of the HAA curing system is low, and the application amount of the HAA system powder coating is rapidly expanded. In recent years, as the price of raw material E-12 epoxy resin of indoor powder coating is high, the powder coating of HAA system has excellent cost advantage and is increasingly used for coating indoor furniture from original outdoor coating.
However, although the HAA system powder coating has excellent combination of properties and low cost, it has a significant disadvantage in that it is difficult to obtain a coating film having a gloss of 90% or more for low gloss decoration because the difference in reactivity of four hydroxyl groups of HAA is small, resulting in a curing speed that is too uniform to be matted.
In order to solve the problem, related companies also research a matting agent product for HAA system, such as a matting agent product prepared by adopting wax powder and an emulsifying agent in CN201910838549.0, but the gloss can only be reduced to 20-30%, and further, the gloss cannot be effectively reduced by continuously increasing the consumption, and the defect of film coating and surface blurring caused by excessive wax powder can be caused. CN202010668166.6 is too many auxiliary agents to be added in the process of preparing powder coating, and two kinds of carboxyl polyesters are simultaneously used, one of which is a polyester resin with high acid value, which is actually equivalent to dry blending extinction, and the stability of the preparation process is poor. While CN201810753591.8 can achieve extinction of 10-20%, since some raw materials contain a large number of functional groups, the raw materials are relatively costly, and it is difficult for downstream customers to use them on a large scale.
Disclosure of Invention
Aiming at the problem that the existing HAA system powder coating has poor extinction when being applied to the direction of indoor decoration powder coating on the basis of cost advantage, the scheme is designed from the connection of a molecular structure, adopts low-cost and carboxyl-intensive polymaleic anhydride and specially selected hydroxyl polyester resin to react, and the hydroxyl in the system has hydroxyl of a hydroxyl polyester chain segment and hydroxyl in an HAA curing agent except obvious difference of the position, activity and steric hindrance of carboxyl in the powder coating prepared by the finally obtained polyester resin, so that obvious carboxyl difference and hydroxyl difference exist in the prepared powder coating on the basis of no need of externally adding an extinction agent, the finally cured film of the powder coating can stably realize the extinction effect of 10-18%, has good surface fineness and other performances, can meet the application requirements, and does not need to use complex raw materials and processes, and has lower cost.
The invention relates to a low-cost and low-light type polyester resin for powder coating, which is polymerized by hydrolyzed polymaleic anhydride aqueous solution, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid and hydroxyl polyester resin.
As a low-cost, low-gloss polyester resin for powder coating, as described above, an aqueous solution of hydrolyzed polymaleic anhydride, HPMA, having a solids content of 55%, for example, commercially available from Shandong Tai and Water treatment technologies Co., ltd; 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 SJ1100, available from Anhui shenjian new materials stock, inc.
The polyester resin for the low-cost and low-light type 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 materials also comprise a certain amount of catalyst and antioxidant.
The dosage of the catalyst is 0.1-0.2% of the total mass of the main raw materials; the catalyst is preferably monobutyl tin oxide.
The dosage of the antioxidant is 0.1-0.2% of the total mass of the main raw materials; the antioxidant is preferably antioxidant 1010, namely 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 hydrolyzed polymaleic anhydride aqueous solution with the formula amount into a head tank for standby;
B. adding terephthalic acid, neopentyl glycol, diethylene glycol and a catalyst in the formula amount into a reaction kettle, heating to 130-135 ℃, fully and uniformly stirring, heating and preserving heat to perform polycondensation reaction;
C. sampling and detecting, namely when the acid value of the polymer is 80-90mgKOH/g, beginning to drop the hydrolyzed polymaleic anhydride aqueous solution in the high-temperature tank, and after the completion of the dropwise addition, gradually heating up and continuing to perform thermal insulation polymerization reaction within 1/3 of the formula amount;
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 hydrolyzed polymaleic anhydride aqueous solution, finishing dropwise adding within 1h, and then continuing to perform thermal insulation polymerization reaction;
E. sampling and detecting, adding antioxidant with the formula amount when the acid value of the polymer reaches 60-70mgKOH/g, starting a vacuum system, and heating to 230-235 ℃ for secondary vacuum polycondensation reaction;
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, melting and mixing at 230-235 ℃ for reaction;
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 while the polymer is hot, cooling the polyester resin, and then crushing and granulating to obtain the polyester resin.
In the step B, the temperature is raised to 175-180 ℃ at a heating rate of 12-15 ℃/h, and the polycondensation reaction is carried out at the temperature; in the step C, the temperature is gradually increased to 220-230 ℃ at the temperature increasing speed of 8-10 ℃; e, controlling the vacuum degree of the vacuum system in the step between-0.095 Mpa and-0.097 Mpa; and F, cooling the polyester resin by using a steel belt with condensed water.
The invention also relates to the use of a low-cost, low-gloss polyester resin for powder coating or a polyester resin obtained by the method in HAA curing systems.
The appearance of the obtained product is colorless transparent particles, the acid value is 38-43mgKOH/g, the hydroxyl value is 8-15mgKOH/g, and the softening point is 115-127 ℃.
The invention has the beneficial effects that:
the polyester resin for the low-cost and low-light type powder coating is mainly prepared by polymerizing a hydrolytic polymaleic anhydride aqueous solution, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid and hydroxyl polyester resin. The polyester resin contains carboxyl polyester resin and hydroxyl polyester resin, wherein the carboxyl polyester structure forms a segmented polymaleic anhydride carboxyl group and isophthalic acid carboxyl group, the polymaleic anhydride carboxyl group is dense and large in steric hindrance, and the hydroxyl in the system has hydroxyl of a hydroxyl polyester chain segment and hydroxyl in an HAA curing agent except obvious difference in position, activity and steric hindrance of carboxyl in the powder coating prepared by the polyester resin, so that obvious carboxyl difference and hydroxyl difference exist in the prepared powder coating on the basis of no need of an external flatting agent, and finally, the cured film of the powder coating can stably realize a flatting effect of 10-18%, has better surface fineness and other performances reaching application requirements, and does not need to use complex raw materials and processes, and has lower cost.
Detailed Description
For the purposes of promoting an understanding of the invention, reference will now be made in detail to various exemplary embodiments of the invention, which should not be considered as limiting the invention in any way, but rather as describing in more detail certain aspects, features and embodiments of the invention.
Among the raw materials, hydrolyzed polymaleic anhydride aqueous solution, namely HPMA, has a solid content of 55% and is purchased from Shandong Tai and water treatment technologies and technologies Co., ltd; the model of the hydroxyl polyester resin is SJ1100, which is purchased from Anhui Shenjian new material Co., ltd; the rest are all common commercial products.
Example 1
The polyester resin for the powder coating comprises the following raw materials in parts by mass:
27 parts of hydrolyzed polymaleic anhydride aqueous solution;
18 parts of terephthalic acid;
16 parts of neopentyl glycol;
6 parts of diethylene glycol;
8 parts of isophthalic acid;
7 parts of hydroxyl polyester resin;
the catalyst is monobutyl tin oxide, and the dosage is 0.1% of the total mass of the main raw materials;
the antioxidant is antioxidant 1010, namely tetra [ methyl-beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] pentaerythritol ester, and the dosage is 0.2% of the total mass of the main raw materials;
the preparation method comprises the following steps:
A. adding the hydrolyzed polymaleic anhydride aqueous solution with the formula amount into a head tank for standby;
B. adding terephthalic acid, neopentyl glycol, diethylene glycol and a catalyst in the formula amount into a reaction kettle, heating to 132 ℃, fully and uniformly stirring, heating to 180 ℃ at a heating rate of 13 ℃/h, and carrying out thermal insulation polycondensation reaction;
C. sampling and detecting, namely when the acid value of the polymer is 85mgKOH/g, beginning to drop the hydrolyzed polymaleic anhydride aqueous solution in the high-temperature tank, finishing the dropwise addition within 1/3 of the formula amount, gradually heating to 230 ℃ at the heating rate of 10 ℃ after finishing the dropwise addition, and then continuing to perform thermal insulation polymerization reaction;
D. when the acid value of the polymer reaches 20mgKOH/g, adding the formula amount of isophthalic acid, simultaneously dropwise adding the rest hydrolyzed polymaleic anhydride aqueous solution, finishing dropwise adding within 1h, and then continuing to perform thermal insulation polymerization reaction;
E. sampling and detecting, adding antioxidant with the formula amount when the acid value of the polymer reaches 65mgKOH/g, starting a vacuum system, controlling the vacuum degree to be-0.096 Mpa, and heating to 233 ℃ for secondary vacuum polycondensation reaction;
E. when the acid value of the polymer reaches 52mgKOH/g, the vacuum is released, the hydroxyl polyester resin with the formula amount is added, and the mixture is stirred, melted and mixed for reaction at 232 ℃;
F. stopping the reaction when the acid value and the hydroxyl value of the polymer reach the following targets, discharging at a high temperature while the polymer is hot, cooling the polyester resin by using a steel belt with condensed water, and then crushing and granulating to obtain the polyester resin.
Finally, the acid value of the prepared polyester resin is 40mgKOH/g, the hydroxyl value is 15mgKOH/g, and the softening point is 116 ℃.
Example 2
The polyester resin for the powder coating comprises the following raw materials in parts by mass:
48 parts of hydrolyzed polymaleic anhydride aqueous solution;
24 parts of terephthalic acid;
28 parts of neopentyl glycol;
8 parts of diethylene glycol;
16 parts of isophthalic acid;
10 parts of hydroxyl polyester resin;
the catalyst is monobutyl tin oxide, and the dosage is 0.1% of the total mass of the main raw materials;
the antioxidant is antioxidant 1010, and the dosage is 0.1% of the total mass of the main raw materials;
the preparation method is the same as in example 1.
Finally, the acid value of the prepared polyester resin was 42mgKOH/g, the hydroxyl value was 13mgKOH/g, and the softening point was 125 ℃.
Example 3
The polyester resin for the powder coating comprises the following raw materials in parts by mass:
38 parts of hydrolyzed 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 dosage is 0.2% of the total mass of the main raw materials;
the antioxidant is antioxidant 1010, and the dosage is 0.2% of the total mass of the main raw materials;
the preparation method is the same as in example 1.
Finally, the acid value of the prepared polyester resin was 39mgKOH/g, the hydroxyl value was 12mgKOH/g, and the softening point was 120 ℃.
Example 4
The polyester resin for the powder coating comprises the following raw materials in parts by mass:
42 parts of hydrolyzed polymaleic anhydride aqueous solution;
18 parts of terephthalic acid;
26 parts of neopentyl glycol;
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 is 0.2% of the total mass of the main raw materials;
the antioxidant is antioxidant 1010, and the dosage is 0.2% of the total mass of the main raw materials;
the preparation method is the same as in example 1.
Finally, the acid value of the prepared polyester resin was 40mgKOH/g, the hydroxyl value was 10mgKOH/g, and the softening point was 122 ℃.
Comparative example 1: a commercially available conventional HAA polyester resin (acid value: 33mgKOH/g, hydroxyl value: 0.8mgKOH/g, softening point 112 ℃ C., model ZJ9505, huang Shanzheng J New Material Co., ltd.).
Application example
The existing powder coating formula is adopted, and the formula is generally as follows in parts by weight:
preparing a paint coating: and uniformly mixing all materials according to the normal HAA system powder coating formula, extruding, tabletting and crushing by a double-screw extruder, and then crushing and sieving the tablets to prepare the powder coating. The powder coating is sprayed on the tinplate base material after surface treatment by adopting an electrostatic spray gun, and is solidified by 180 ℃/20min, thus obtaining the coating.
Coating index detection basis: GB/T21776-2008 guide the detection criteria for powder coatings and their coatings. The gloss of the coating is tested by adopting a 60-degree angle; the leveling grade is carried out by adopting a PCI grading method, and the larger the number is, the better the leveling is.
Table 1 coating film properties of examples and comparative examples
As can be seen from Table 1, the gloss of the product prepared by the scheme of the invention can reach 10-15% under the condition of no external matting agent, the difference of carboxyl type, position and activity in the polyester chain segment is fully utilized, meanwhile, the difference of curing speed is finally realized by means of the difference of hydroxyl type and activity to matting, the curing time is prolonged to 20min to achieve the effects of full curing and high leveling, the cost of raw materials selected by the product of the invention is lower, single polyester resin is prepared under a special process, the application is convenient, and the prepared powder coating has good stability.
Comparative example 1 uses a polyester resin of a general commercial HAA system, and has a gloss of 90% or more without adding an additional matting agent, and it is difficult to obtain a low-gloss powder coating having excellent decorative properties.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. And obvious variations or modifications thereof are contemplated as falling within the scope of the present invention.
Claims (7)
1. A low-cost, low-gloss polyester resin for powder coating, characterized in that the raw materials include aqueous solution of hydrolyzed polymaleic anhydride, terephthalic acid, neopentyl glycol, diethylene glycol, isophthalic acid, hydroxyl polyester resin, and are obtained by polymerization thereof;
the polyester resin 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 materials also comprise a catalyst and an antioxidant;
wherein the solid content of the hydrolyzed polymaleic anhydride aqueous solution is 55%; the hydroxyl value of the hydroxyl polyester resin is 38-43mgKOH/g, and the glass transition temperature Tg is 62-65 ℃;
the preparation method of the polyester resin comprises the following steps:
A. adding the hydrolyzed polymaleic anhydride aqueous solution with the formula amount into a head tank for standby;
B. adding terephthalic acid, neopentyl glycol, diethylene glycol and a catalyst in the formula amount into a reaction kettle, heating to 130-135 ℃, fully and uniformly stirring, heating and preserving heat to perform polycondensation reaction;
C. sampling and detecting, namely when the acid value of the polymer is 80-90mgKOH/g, beginning to drop the hydrolyzed polymaleic anhydride aqueous solution in the high-temperature tank, and after the completion of the dropwise addition, gradually heating up and continuing to perform thermal insulation polymerization reaction within 1/3 of the formula amount;
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 hydrolyzed polymaleic anhydride aqueous solution, finishing dropwise adding within 1h, and then continuing to perform thermal insulation polymerization reaction;
E. sampling and detecting, adding antioxidant with the formula amount when the acid value of the polymer reaches 60-70mgKOH/g, starting a vacuum system, and heating to 230-235 ℃ for secondary vacuum polycondensation reaction; when the acid value of the polymer reaches 50-55mgKOH/g, releasing the vacuum, adding the hydroxyl polyester resin with the formula amount, stirring, melting and mixing at 230-235 ℃ for reaction;
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 while the polymer is hot, cooling the polyester resin, and then crushing and granulating to obtain the polyester resin.
2. A low cost, low profile polyester resin for powder coating as recited in claim 1, wherein the catalyst is monobutyl tin oxide.
3. A low cost, low profile polyester resin for powder coating as recited in claim 1, wherein the antioxidant is antioxidant 1010.
4. The polyester resin for low-cost and low-gloss powder coating according to claim 1, wherein the polycondensation is carried out by heating to 175 to 180℃at a heating rate of 12 to 15℃per hour in step B of the production method.
5. The polyester resin for low-cost, low-gloss powder coating according to claim 1, wherein in the step C of the production method, the temperature is gradually increased to 220 to 230℃at a temperature increase rate of 8 to 10 ℃.
6. The polyester resin for low-cost, low-gloss powder coating according to claim 1, wherein in the step E of the production method, the vacuum degree of the vacuum system 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.
7. Use of a low-cost, low-gloss polyester resin for powder coatings according to any of claims 1 to 6 in HAA curing systems.
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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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