CN109232866A - A kind of polyester resin and the preparation method and application thereof - Google Patents
A kind of polyester resin and the preparation method and application thereof Download PDFInfo
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- CN109232866A CN109232866A CN201810943214.0A CN201810943214A CN109232866A CN 109232866 A CN109232866 A CN 109232866A CN 201810943214 A CN201810943214 A CN 201810943214A CN 109232866 A CN109232866 A CN 109232866A
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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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
-
- 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
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Sustainable Development (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention discloses a kind of polyester resin and the preparation method and application thereof.The acid value of the polyester resin is 30~80mgKOH/g, glass transition temperature is 40~80 DEG C, 200 DEG C of melt viscosities are 1000~10000mPas, softening point is 80~123 DEG C, 180 DEG C of reactivity are 100~300s, number-average molecular weight be 3000~7000, the polyester resin by polyester waste material, polyalcohol, polyacid, end-capping reagent, be prepared.The above-mentioned performance of polyester resin of the invention has large range of variation, thus has wider array of applicability；Meanwhile the present invention prepares polyester resin using polyester waste material, preparation condition is mild, and no coupling product generates in preparation process, and pure polyester resin is prepared in single step reaction completely；The powdery paints plate face appearance prepared by polyester resin of the invention preferably, coating mechanical performance and adhesive force is excellent, chemical-resistance and salt tolerant object, boiling excellent performance, be suitable for various indoor field of coating.
Description
Technical field
The present invention relates to material recoveries to recycle field, and in particular to a kind of polyester resin and the preparation method and application thereof.
Background technique
With the fast development of high molecular material, obtained in every field by the high molecular material of representative of polyester plastics
Large-scale application, dosage is maximum especially in plastic bottle and engineering plastics, these materials can generate largely after use
Waste, and, it is long since there is polyester plastics chemical stability, corrosion resistance, electrical insulating property, thermal insulation to be not easy nature resolution
Phase sets to stay and can cause greatly to damage to environment in environment, is unfavorable for sustainable development；It meanwhile with crude oil or natural gas being original
The high molecular material cost of material is continuously increased, and resource is constantly reduced, and the recycle and reuse of polyester waste material is made to become one
Emerging topic and urgent problem to be solved.
Recycling and reusing about polyester waste material is concentrated mainly on the side such as polyester thermosol, polyurethane elastomer and water-reducing agent
To, such as: CN101760163A, CN107163892A and CN101434821A, which report to have arrived, utilizes polyester waste material preparation hot melt
The method of glue, CN101851326A report it is a kind of prepare method for preparing polyurethane elastic body using pet waste,
CN103274628A discloses a kind of method using waste PET plastics-production water-reducing agent, and degrades about using polyester waste material
The research for preparing powdery paints is relatively fewer, due in the production of polyester resin for powder coating, raw material types and life
Raw material types used in production polyester plastics are essentially identical, and preparing polyester resin for powder coating using polyester waste material degradation is one
The direction of a worth research, CN106065068A, which is disclosed, prepares powdery paints with pure polyester using polyester waste material；
CN101177503A, which is disclosed, to carry out recycling to waste polyester using composite heating method and prepares powdery paints polyester, but benefit at present
The performance changes ranges such as acid value, melt viscosity, the glass transition temperature of polyester resin prepared with polyester waste material are relatively narrow, uncomfortable
In extensive use, meanwhile, that there are glycolysis temperatures is higher for the above method, alcoholysis reaction is incomplete, by-product is more or needs to use
To heating instruments such as infrared heating case, micro-wave ovens, on the one hand influences the recovery utilization rate of polyester waste material or its by-product causes newly
Environmental pollution, on the other hand be also unfavorable for practical operation, limit it and be mass produced.
Summary of the invention
The purpose of the present invention is to provide a kind of polyester resin and the preparation method and application thereof.
The present invention prepares polyester resin using polyester waste material, and the properties of the polyester resin have large range of change
Change, be able to satisfy the demand of different acid values, glass transition temperature and melt viscosity, there is wider applicability；Meanwhile the system
Preparation Method is simple, efficient, no coupling product generates；In addition, the powdery paints prepared by the polyester resin have plate face appearance preferably,
The advantages that coating mechanical performance and excellent adhesive force.
Specifically, one of the objects of the present invention is to provide a kind of polyester resin, the acid value of the polyester resin is 30~
80mgKOH/g, glass transition temperature are 40~80 DEG C, and 200 DEG C of melt viscosities are 1000~10000mPas, and softening point is
80~123 DEG C, 180 DEG C of reactivity are 100~300s, and number-average molecular weight is 3000~7000, and the polyester resin is by following raw material
It is prepared: polyester waste material, polyalcohol, polyacid, end-capping reagent.
Preferably, above-mentioned polyester resin is prepared by the raw material of following mass percent: 3~45% polyester waste materials, 20
~40% polyalcohol, 25~55% polyacids, 3~25% end-capping reagents.
It is highly preferred that above-mentioned polyester resin is prepared by the raw material of following mass percent: 5~40% polyester waste materials,
23~35% polyalcohols, 28~50% polyacids, 5~20% end-capping reagents.
Preferably, above-mentioned polyester waste material is selected from polyethylene terephthalate, polybutylene terephthalate, gathers to benzene two
At least one of formic acid Isosorbide-5-Nitrae-cyclohexane dicarboxylates.
Preferably, polyalcohol is selected from neopentyl glycol, ethylene glycol, diethylene glycol (DEG), 2- methyl-1,3-propanediol, trihydroxy methyl third
At least one of alkane, trimethylolethane.
Preferably, polyacid is selected from least one of terephthalic acid (TPA), M-phthalic acid, adipic acid.
Preferably, end-capping reagent is selected from least one of trimellitic anhydride, adipic acid.
Another object of the present invention is to provide the preparation methods of above-mentioned polyester resin, include the following steps:
1) polyester waste material, polyalcohol and alcoholysis catalysts are subjected under conditions of starvation alcoholysis reaction, obtain alcoholysis
Product；
2) polyacid and esterification catalyst are added in above-mentioned alcoholysis product by starvation, are carried out esterification, are obtained ester
Change product；
3) esterification products are subjected to polycondensation reaction, obtain polycondensation product；
4) end-capping reagent is added in starvation in polycondensation product, carries out end capping reaction, obtains polyester resin.
Preferably, the temperature of alcoholysis reaction is 140~190 DEG C in step 1), reacts clear to reaction system at this temperature
It is clear transparent, it may be assumed that polyester waste material fully reacting；Preferably, the time of alcoholysis reaction is 3~8h.
It is highly preferred that the temperature of alcoholysis reaction is 160~180 DEG C in step 1), reacted at this temperature to reaction system
It is Clear & Transparent, it may be assumed that polyester waste material fully reacting, it is preferable that the time of alcoholysis reaction is 4~6h.
Preferably, the mass percent of the alcoholysis catalysts in step 1) is 0.05~0.3%；Preferably, alcoholysis is catalyzed
Agent is selected from Titanium series catalyst；It is highly preferred that alcoholysis catalysts are in C-94, CA135, Hombifast PC and STiC-01
It is at least one.
Preferably, the temperature of the esterification in step 2) is 220~250 DEG C, and reaction to not further water distillates；
Preferably, the time of esterification is 3~6h.
It is highly preferred that the temperature of the esterification in step 2) is 230~240 DEG C, reaction to not further water evaporates
Out；Preferably, the time of esterification is 3.5~5h.
Preferably, the mass percent of the esterification catalyst in step 2) is 0~0.3%；Preferably, esterification catalyst selects
From organic tin catalyst, it is highly preferred that esterification catalyst is selected from Mono-n-butyltin, Dibutyltin oxide, dibutyl tin two
At least one of laurate and tin oxalate.
Preferably, when the mass percent of alcoholysis catalysts is 0.05~0.15%, the quality percentage of esterification catalyst
Number is 0.01~0.3%, it is highly preferred that the mass percent of esterification catalyst is 0.01~0.15%；When alcoholysis catalysts
When mass percent is 0.15~0.3%, the mass percent of esterification catalyst can 0 or to be greater than 0 and less than 0.3%,
It is highly preferred that the mass percent of esterification catalyst can be 0 or to be greater than 0 and less than 0.15%.
In step 3) until vacuum polycondensation to the acid value and melt viscosity for reaching required, the present invention is to reach needed for the present invention
Acid value and melting viscosity, it is preferable that the vacuum degree of step 3) is 0.08~0.1MPa, and the temperature of polycondensation reaction is 200~230
℃；Preferably, the time of polycondensation reaction is 1~3h.
It is highly preferred that the vacuum degree of step 3) is 0.086~0.096MPa, the temperature of polycondensation reaction is 217~228 DEG C；
It is highly preferred that the time of polycondensation reaction is 1.5~2.5h.
Preferably, end capping reaction to acid value is 30~80mg KOH/g in step 4), 200 DEG C of melt viscosities are 1000~
10000mPa·s。
Preferably, the temperature of end capping reaction is 190~230 DEG C in step 4).
Preferably, the time of end capping reaction is 0.5~1h in step 4).
Preferably, further include the steps that auxiliary agent is added after end capping reaction in step 4).
Preferably, above-mentioned auxiliary agent in tert-butylamine, benzyltriethylammoinium chloride and benzyl triethyl ammonium bromide extremely
Few one kind.
The present invention also provides a kind of powdery paints.
The powdery paints includes above-mentioned polyester resin.
The beneficial effects of the present invention are:
1, the acid value of polyester resin of the invention is 30~80mg KOH/g, and glass transition temperature is 40~80 DEG C, soft
Changing point is 80~123 DEG C, and 200 DEG C of melt viscosities are 1000~10000mPas, and 180 DEG C of reactivity are 100~300s, and number is equal
Molecular weight is 3000~7000, it may be assumed that the above-mentioned performance of polyester resin of the invention has large range of variation, thus has more
Wide applicability.
2, the present invention prepares polyester resin using polyester waste material, and preparation condition is mild, and no coupling product is raw in preparation process
At pure polyester resin is prepared in single step reaction completely, avoids pollution of the new by-product to environment, or increase to by-product
The step of reason, or lead to problems such as Reclaim of PET Scrap rate low.
3, the powdery paints plate face appearance prepared by polyester resin of the invention preferably, coating mechanical performance and adhesive force it is excellent
Good, chemical-resistance and salt tolerant object, boiling excellent performance are suitable for various indoor field of coating.
Specific embodiment
Enumerate embodiment further below with the present invention will be described in detail.It will similarly be understood that following embodiment is served only for this
Invention is further described, and should not be understood as limiting the scope of the invention, those skilled in the art are according to the present invention
Some nonessential modifications and adaptations that the principle of elaboration is made all belong to the scope of protection of the present invention.Following specific works of example
Skill parameter etc. is also only an example in OK range, i.e. those skilled in the art can do suitable model by the explanation of this paper
Interior selection is enclosed, and does not really want to be defined in hereafter exemplary specific data.
The following describes the present invention in detail with reference to examples, and the component of each embodiment polyester resin see the table below 1 (such as nothing
The unit for especially indicating following components is g):
Table 1
The performance of the polyester resin of above-described embodiment 1~6 see the table below 2:
Table 2
As shown in Table 2: the present invention using polyester waste material preparation polyester resin acid value variable range be 30~
80mgKOH/g, 200 DEG C of melt viscosities variable range be the variable range of 1000~10000mPas, glass transition temperature
It is 40~80 DEG C, it can be seen that: different acid values, melt viscosity and the glass transition of larger range variation may be implemented in the present invention
The preparation of the polyester resin of temperature, thus there is wider array of applicability, it may be assumed that the powdery paints production for meeting different performance can be prepared
Product.
The preparation step of the polyester resin of Examples 1 to 6 is following, and (component and its proportion of different embodiments are by upper table 1
Addition):
1) alcoholysis reaction: by polyester waste material, polyalcohol and the alcoholysis catalysts in upper table 1, alcohol is carried out under nitrogen protection
Solution reaction, the temperature of alcoholysis reaction are 140~190 DEG C, and the time of alcoholysis reaction is 3~8h, obtain alcoholysis product；
2) esterification: under nitrogen protection, by upper table 1 polyacid and esterification catalyst be added in step 1)
It in alcoholysis product, is warming up to 220~250 DEG C and carries out esterification dehydration, the reaction time is 3~6h, obtains esterification products；
3) polycondensation reaction: by the esterification products of step 2) under 200~230 DEG C and 0.08~0.1MPa of vacuum degree, into
The time of row polycondensation reaction, polycondensation reaction is 1~3h, obtains polycondensation product；
4) end capping reaction: under nitrogen protection, the end-capping reagent in upper table 1 is added in the polycondensation product of step 3) and is carried out
End capping reaction, the temperature of end capping reaction are 190~230 DEG C, and the time of end capping reaction is 0.5~2h, at this point, its acid value be 30~
80mgKOH/g, 200 DEG C of melt viscosities are 1000~10000mPas, and appropriate tert-butylamine, benzyltriethylammoinium chloride is added
Or benzyl triethyl ammonium bromide auxiliary agent, it stirs evenly, obtains polyester resin.
By the performance test for the powdery paints that the polyester resin of Examples 1 to 6 is made:
By the polyester resin of the embodiment of the present invention 1~6 respectively with curing agent (epoxy resin (E-12)), levelling agent
GLP588, titanium dioxide, barium sulfate, optical brightener (701) and degasser (styrax) according to the form below 3 ratio weigh up after mix (note: such as
Without special instruction, the component unit in table 3 be g), it is extrusion after being melted with screw extruder, tabletting, broken, after by piece feed powder
Powdery paints is made in broken sieving, and polyester resin 1,2,3,4,5,6 described in table 3 is expressed as the polyester tree of Examples 1 to 6
Rouge；
Electrostatic gun is respectively adopted in the powdery paints that the polyester resin of Examples 1 to 6 is made and is sprayed on surface treated
On the metal plate of (phosphatization), coating thickness is about 80 μm, through 180 DEG C/15min solidify, after perform the following performance tests, test knot
Fruit is shown in Table 4:
1, gloss is tested according to GB/T9754-2007；
2, impact is tested according to GB/T1732-1993；
3, adhesive force is tested according to GB/T9286-1998；
4, the curved experiment of T is tested according to GB/T 30791-2014；
5, neutral salt spray test (500h) is tested according to GB/T1771-91.
Table 3
The performance of the powdery paints prepared by the polyester resin of Examples 1 to 6 is shown in Table 4:
Table 4
As shown in Table 4: polyester resin of the invention and the powdery paints of epoxy resin (E-12) preparation have suitably instead
Activity is answered, the coating after solidification has good plate face appearance (smooth), mechanical performance and adhesive force；Meanwhile coating
Other preferable comprehensive performances, such as boiling performance and salt spray resistance are shown, which can apply to well
The powdery paints of various interior field of coating.
Claims (10)
1. a kind of polyester resin, it is characterised in that: the acid value of the polyester resin is 30~80mgKOH/g, glass transition temperature
Degree is 40~80 DEG C, and 200 DEG C of melt viscosities are 1000~10000mPas, and softening point is 80~123 DEG C, and 180 DEG C of reactivity are
100~300s, number-average molecular weight are 3000~7000, and the polyester resin is prepared by following raw material: polyester waste material, polynary
Alcohol, polyacid, end-capping reagent.
2. polyester resin according to claim 1, it is characterised in that: the polyester resin by following mass percent original
Material is prepared: 3~45% polyester waste materials, 20~40% polyalcohols, 25~55% polyacids, 3~25% end-capping reagents.
3. polyester resin according to claim 1, it is characterised in that: the polyester waste material is selected from poly terephthalic acid second two
At least one of ester, polybutylene terephthalate, poly terephthalic acid Isosorbide-5-Nitrae-cyclohexane dicarboxylates；Preferably, polyalcohol
In neopentyl glycol, ethylene glycol, diethylene glycol (DEG), 2- methyl-1,3-propanediol, trimethylolpropane, trimethylolethane extremely
Few one kind；Preferably, polyacid is selected from least one of terephthalic acid (TPA), M-phthalic acid, adipic acid；Preferably, it blocks
Agent is selected from least one of trimellitic anhydride, adipic acid.
4. a kind of described in any item preparation methods of polyester resin of claims 1 to 3, characterized by the following steps:
1) polyester waste material, polyalcohol and alcoholysis catalysts are subjected under conditions of starvation alcoholysis reaction, obtain alcoholysis product；
2) polyacid and esterification catalyst are added in above-mentioned alcoholysis product by starvation, are carried out esterification, must be esterified production
Object；
3) esterification products are subjected to polycondensation reaction, obtain polycondensation product；
4) end-capping reagent is added in starvation in polycondensation product, carries out end capping reaction, obtains polyester resin.
5. the preparation method according to claim 4, it is characterised in that: the temperature of alcoholysis reaction is 140~190 in step 1)
℃。
6. the preparation method according to claim 4, it is characterised in that: the mass percent of the alcoholysis catalysts in step 1)
It is 0.05~0.3%；Preferably, alcoholysis catalysts are selected from Titanium series catalyst.
7. the preparation method according to claim 4, it is characterised in that: the mass percent of the esterification catalyst in step 2)
It is 0~0.3%；Preferably, esterification catalyst is selected from organic tin catalyst.
8. the preparation method according to claim 4, it is characterised in that: vacuum degree is 0.08~0.1MPa, contracting in step 3)
The temperature of poly- reaction is 200~230 DEG C.
9. the preparation method according to claim 4, it is characterised in that: in step 4) end capping reaction to acid value be 30~
80mgKOH/g, 200 DEG C of melt viscosities are 1000~10000mPas.
10. a kind of powdery paints, it is characterised in that: the powdery paints includes claims 1 to 3 any one claim institute
The polyester resin stated.
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| CN201810943214.0A CN109232866A (en) | 2018-08-17 | 2018-08-17 | A kind of polyester resin and the preparation method and application thereof |
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| CN201810943214.0A CN109232866A (en) | 2018-08-17 | 2018-08-17 | A kind of polyester resin and the preparation method and application thereof |
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| CN109749067A (en) * | 2019-03-05 | 2019-05-14 | 安徽永利新材料科技有限公司 | A kind of polyester resin for powder coating and preparation method thereof that flexibility is excellent |
| CN109749067B (en) * | 2019-03-05 | 2021-01-26 | 安徽永利新材料科技有限公司 | Polyester resin with excellent flexibility for powder coating and preparation method thereof |
| CN110467874A (en) * | 2019-08-20 | 2019-11-19 | 德州名将工贸有限公司 | A kind of preparation process of thermosetting powder coating modified polyester resin |
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