CN110483751A - A kind of HAA system extinction type polyester resin and the preparation method and application thereof - Google Patents
A kind of HAA system extinction type polyester resin and the preparation method and application thereof Download PDFInfo
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- CN110483751A CN110483751A CN201810753591.8A CN201810753591A CN110483751A CN 110483751 A CN110483751 A CN 110483751A CN 201810753591 A CN201810753591 A CN 201810753591A CN 110483751 A CN110483751 A CN 110483751A
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- polyester resin
- extinction type
- haa
- type polyester
- haa system
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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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—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
- 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
- C09D5/033—Powdery paints characterised by the additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
HAA system extinction type polyester resin of the present invention, with terephthalic acid (TPA), tetrahydrophthalic acid, 2- amino -4, 6- dihydroxy-pyrimidine, neopentyl glycol, 1, 10- decanediol, diacetone-D-mannital, 1, 4, 5, 8- naphthalenetetracarbacidic acidic acid anhydride, oreinol diacid, Trimethyl citrate is raw material, by cooperating and acting synergistically between above-mentioned each component, so that there are molecular weight distributions is uneven for finally obtained polyester resin, and the diverse feature of polyacid of sealing end, therefore, different terminal functional group polyester resin with HAA when solidifying, its reactivity differs greatly, prevent solidification process is carried out from synchronizing, and then the film coated surface after solidifying is caused to shrink, lustrous surface is effectively lower.Experimental data is shown, when extinction type powdery paints preparation of the extinction type polyester resin for HAA system is made in the present invention, the film of available glossiness < 15%, and achieve excellent comprehensive performance.
Description
Technical field
The invention belongs to powder coating technology fields, and in particular to a kind of HAA system extinction type polyester resin goes forward side by side one
Open preparation method is walked, and its is used to prepare the purposes of HAA system powdery paints.
Background technique
Powdery paints is a kind of 100% solid powder without organic solvent, it is different from oil paint and water paint,
Not using solvent or water as decentralized medium when coating, but using air as decentralized medium, it is uniformly coated on workpiece surface, is passed through
A kind of new type environment friendly coating of one layer of film with specific use is formed after heating.Powdery paints has VOC free, environmental protection, section
Can, the advantages that construction efficiency height and application range is wide, and the advantages that, environmental protection economic with it, brilliant efficient and performance, just gradually replace
For organic solvent type coatings, become the important development direction in coating industry, is always maintained at faster growth rate.Polyesters
Powdery paints more with its excellent durability, dicoration and processing forming the features such as, be widely used in field of coating.
Matt powder coating is a kind of powdery paints for being usually used in indoor and outdoor coating, has vision soft, painting effect is stopped
Not busy, fashion advantage.Currently, sub-smooth type powdery paints is to obtain matt effect by addition special auxiliary agent or hybrid resin
's.Its principle is to control the difference for solidifying speed of different component or in which a part and film is caused to shrink difference, and then shape
At irregular surface texture.So-called delustring is exactly so that the glossiness of film coated surface is lowered using certain method.In conjunction with painting
The factor of mechanism and influence gloss that film surface gloss generates, it is believed that delustring is exactly to destroy film using various means
Slickness increases the asperity of film coated surface, reduces reflection of the film coated surface to light.Extinction method is generally divided into physics
Delustring and chemical quenching two ways: physics delustering agent is that delustering agent is added to keep coating uneven in the generation of film forming procedure surface
Increase the scattering to light and reduce and reflects；Chemical quenching, which is positioned against in coating, to be introduced some for example poly- propyl ester grafting material classes and can inhale
Structure or the group of light are received to obtain low gloss.
Traditional powdery paints polyester mostly be carboxyl polyester resin either hydroxy polyester resin, but the system polyester without
Method realizes the self-curing of polyester system, and institute's corresponding curing agent of addition in need realizes solidification.Currently, outdoor pure polyester powder
Coating curing agent is mainly based on TGIC and HAA, but discovered in recent years TGIC can be caused to be mutated and be had to human body reproduction cell
Heredity, most of country, European Union have been forbidden to use TGIC as curing agent.Therefore, development uses environment-friendly type HAA system powder
Last coating has been trend of the times.Since the degree of functionality of HAA curing agent is higher, so that its curing activity is higher, curing rate is fast, and
Curing degree is uniform, but the glossiness that film coated surface is easily led to when its defect is higher, and is more difficult to get low gloss (< 20%)
Film is unfavorable for the preparation of sub-smooth type powdery paints.Therefore, a kind of extinction type polyester resin tool suitable for HAA system is developed
There is positive meaning.
Summary of the invention
For this purpose, going forward side by side technical problem to be solved by the present invention lies in a kind of HAA system extinction type polyester resin is provided
One step discloses preparation method；
Second technical problem that the present invention solves is to provide a kind of extinction type polyester resin and is used to prepare HAA type powder
The purposes of coating.
In order to solve the above technical problems, a kind of HAA system extinction type polyester resin of the present invention, with the polyester
The total amount meter of resin prepares the raw material components that raw material includes following molar percentage:
Preferably, the HAA system extinction type polyester resin, in terms of the total amount of the polyester resin, preparation is former
Material includes the raw material components of following molar percentage:
The HAA system extinction type polyester resin, further includes catalyst, and the mole dosage of the catalyst accounts for described
The 0.1-0.3% of raw material components integral molar quantity.
The catalyst includes Bis(lauroyloxy)dioctyltin.
The HAA system extinction type polyester resin, further includes antioxidant, and the mole dosage of the antioxidant accounts for described
The 0.3-0.5% of raw material components integral molar quantity.
The antioxidant includes antioxidant 702.
The invention also discloses a kind of methods for preparing the HAA system extinction type polyester resin, including walk as follows
It is rapid:
(1) a selected amount of 2- amino -4,6- dihydroxy-pyrimidine, neopentyl glycol, 1,10- decanediol, diacetone-D- are taken
Mannitol mixing, and temperature is controlled lower than 135 DEG C of progress heating meltings；
(2) a selected amount of terephthalic acid (TPA) and tetrahydrophthalic acid are added in Xiang Shangshu mixed material, and is added
A selected amount of catalyst is warming up to 200-210 DEG C of progress insulation reaction under nitrogen protection；Nothing is then gradually warming up to obviously to evaporate
Until object steams out, and the acid value of reactant is less than 25mgKOH/g；
(3) a selected amount of antioxidant is added, keeps the vacuum degree 2-8h of 40-60mmHg, facilitates the formation of polyester resin, to
Acid value stops pulling vacuum when being reduced to 15mgKOH/g or less；
(4) when material being cooled to 200-210 DEG C, and a selected amount of Isosorbide-5-Nitrae is added, 5,8- naphthalenetetracarbacidic acidic acid anhydrides, 5- first
Base isophthalic acid and Trimethyl citrate, and be to slowly warm up to 240 DEG C and end capping reaction 3-9h is carried out to polyester resin, to reactant
Acid value be 26-34mgKOH/g when stop reaction, then material is cooled to 200 DEG C, and high temperature discharging while hot, through cold
But, be crushed, be granulated to get.
In the step (2), the heating step is to be rapidly heated in 2h to 200-210 DEG C.
The invention also discloses the HAA systems to be used to prepare the purposes of powdery paints with extinction type polyester resin.
The powdery paints is HAA system polyester powder coating.
HAA system extinction type polyester resin of the present invention, with terephthalic acid (TPA), tetrahydrophthalic acid, 2- ammonia
Base -4,6- dihydroxy-pyrimidine, neopentyl glycol, 1,10- decanediol, diacetone-D-mannital, 1,4,5,8 naphthalenetetracarboxylic acid acid anhydride,
Oreinol diacid, Trimethyl citrate are raw material, since the activity of used polyacid and polyalcohol is different, are such as added
The carboxyl-reactive difference of the terephthalic acid (TPA) with armaticity that adds and the not tetrahydrophthalic acid of armaticity is larger, passes through
It cooperates and acts synergistically between above-mentioned each component, and the control for technical process, so that finally obtained polyester tree
That there are molecular weight distributions is uneven for rouge, and contains amido in molecule segment, the polyacid type finally blocked it is also different (such as Isosorbide-5-Nitrae,
5,8- naphthalenetetracarbacidic acidic acid anhydrides, oreinol diacid and Trimethyl citrate sealing end), due to final polyester segment obtained and sealing end
Group mainly includes that the form of amido, acid anhydrides, carboxyl and methyl esters exists, therefore, poly- containing different functional groups in molecular structure
When solidifying with HAA, reactivity differs greatly ester resin, prevent solidification process is carried out from synchronizing, and then causes to solidify
Film coated surface afterwards is shunk, and lustrous surface is effectively lower.Experimental data shows that the present invention is made extinction type polyester resin and uses
When the extinction type powdery paints preparation of HAA system, the film of available glossiness < 15%, and achieve excellent synthesis
Performance.
Specific embodiment
Embodiment 1
HAA system extinction type polyester resin described in the present embodiment prepares raw material in terms of the total amount of the polyester resin
Raw material components including following mole:
The present embodiment preparation HAA system method of extinction type polyester resin, includes the following steps:
(1) a selected amount of 2- amino -4,6- dihydroxy-pyrimidine, neopentyl glycol, 1,10- decanediol, diacetone-D- are taken
Mannitol mixing, and temperature is controlled lower than 135 DEG C of progress heating meltings；
(2) a selected amount of terephthalic acid (TPA) and tetrahydrophthalic acid are added in Xiang Shangshu mixed material, and is added
A selected amount of catalyst is rapidly heated under nitrogen protection to 200-210 DEG C of progress insulation reaction in 2h；Then gradually heat up
It is steamed to without obvious distillate, and the acid value of reactant is less than until 25mgKOH/g；And control the reaction temperature of whole process not
More than 245 DEG C；
(3) a selected amount of antioxidant is added, keeps the vacuum degree 2-8h of 40-60mmHg, facilitates the formation of polyester resin, to
Acid value stops pulling vacuum when being reduced to 15mgKOH/g or less；
(4) when material being cooled to 200-210 DEG C, and a selected amount of Isosorbide-5-Nitrae is added, 5,8- naphthalenetetracarbacidic acidic acid anhydrides, 5- first
Base isophthalic acid and Trimethyl citrate, and be to slowly warm up to 240 DEG C and end capping reaction 3-9h is carried out to polyester resin, to reactant
Acid value be 26-34mgKOH/g when stop reaction, then material is cooled to 200 DEG C, and high temperature discharging while hot, through cold
But, be crushed, be granulated to get.
Through detecting, extinction type polyester resin appearance prepared by the present embodiment is colorless and transparent particle, the polyester tree
The acid value of rouge is 32mgKOH/g, and softening point is 117 DEG C.
Embodiment 2
HAA system extinction type polyester resin described in the present embodiment prepares raw material in terms of the total amount of the polyester resin
Raw material components including following mole:
The preparation method is the same as that of Example 1 with extinction type polyester resin for HAA system described in the present embodiment.
Through detecting, extinction type polyester resin appearance prepared by the present embodiment is colorless and transparent particle, the polyester tree
The acid value of rouge is 30mgKOH/g, and softening point is 120 DEG C.
Embodiment 3
HAA system extinction type polyester resin described in the present embodiment prepares raw material in terms of the total amount of the polyester resin
Raw material components including following mole:
The preparation method is the same as that of Example 1 with extinction type polyester resin for HAA system described in the present embodiment.
Through detecting, extinction type polyester resin appearance prepared by the present embodiment is colorless and transparent particle, the polyester tree
The acid value of rouge is 34mgKOH/g, and softening point is 112 DEG C.
Embodiment 4
HAA system extinction type polyester resin described in the present embodiment prepares raw material in terms of the total amount of the polyester resin
Raw material components including following mole:
The preparation method is the same as that of Example 1 with extinction type polyester resin for HAA system described in the present embodiment.
Through detecting, extinction type polyester resin appearance prepared by the present embodiment is colorless and transparent particle, the polyester tree
The acid value of rouge is 26mgKOH/g, and softening point is 108 DEG C.
Embodiment 5
HAA system extinction type polyester resin described in the present embodiment prepares raw material in terms of the total amount of the polyester resin
Raw material components including following mole:
The preparation method is the same as that of Example 1 with extinction type polyester resin for HAA system described in the present embodiment.
Through detecting, extinction type polyester resin appearance prepared by the present embodiment is colorless and transparent particle, the polyester tree
The acid value of rouge is 29mgKOH/g, and softening point is 115 DEG C.
Comparative example 1
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference is only that without containing to benzene two
Formic acid.
Through detecting, the acid value 27mgKOH/g of polyester resin prepared by this comparative example, 110 DEG C of softening point.
Comparative example 2
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference is only that without containing tetrahydro neighbour
Phthalic acid.
Through detecting, the acid value 26mgKOH/g of polyester resin prepared by this comparative example, 105 DEG C of softening point.
Comparative example 3
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference is only that without containing 2- amino-
4,6- dihydroxy-pyrimidine.
Through detecting, the acid value 32mgKOH/g of polyester resin prepared by this comparative example, 107 DEG C of softening point.
Comparative example 4
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference was only that without containing 1, the 10- last of the ten Heavenly stems
Glycol.
Through detecting, the acid value 33mgKOH/g of polyester resin prepared by this comparative example, 124 DEG C of softening point.
Comparative example 5
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference is only that without containing diacetone-
D-mannital.
Through detecting, the acid value 34mgKOH/g of polyester resin prepared by this comparative example, 110 DEG C of softening point.
Comparative example 6
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference is only that without containing Isosorbide-5-Nitrae, and 5,
8- naphthalenetetracarbacidic acidic acid anhydride.
Through detecting, the acid value 26mgKOH/g of polyester resin prepared by this comparative example, 111 DEG C of softening point.
Comparative example 7
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference is only that without containing 5- methyl
Isophthalic acid.
Through detecting, the acid value 28mgKOH/g of polyester resin prepared by this comparative example, 112 DEG C of softening point.
Comparative example 8
The raw material composition of polyester resin described in this comparative example is same as Example 5, and difference is only that without containing citric acid
Trimethyl.
Through detecting, the acid value 30mgKOH/g of polyester resin prepared by this comparative example, 114 DEG C of softening point.
Experimental example
Extinction type polyester resin made from 1-5 of the embodiment of the present invention and comparative example 1-8 is taken respectively, is grouped as according to following group
Carry out the preparation of HAA type polyester powder coating:
And with the conventional use of polyester resin of HAA powder coating systems (acid value 32mgKOH/g, softening point in the prior art
120 DEG C) replace extinction type polyester resin of the present invention as a comparison case 9.
Each material is mixed according to HAA system with the formula of extinction type powdery paints by the polyester resin respectively, is used
Double screw extruder extrusion, is crushed tabletting, then sheet stock pulverizes and sieves, powdery paints is made.Powdery paints uses electrostatic
Rifle is sprayed on the tinplate substrate after surface treated, is solidified through 180 DEG C/15min to get corresponding powdery paints is arrived
Coating.
Coating Indexs measure is remembered according to GB/T 21776-2008 " the examination criteria guide of powdery paints and its coating "
Every detection data is recorded in the following table 1.
1 performance powder coating detection data of table
Data comparison can be seen that extinction type polyester resin of the present invention from table 1, pass through phase interworking between each component
It closes and acts synergistically, keep finally obtained polyester resin uneven in molecular weight distribution, and the polyacid type blocked is different, into
And reactivity differs greatly when gained polyester resin being made to be HAA solidification, solidification cannot synchronize progress, lead to the painting after solidifying
Film surface is shunk, and lustrous surface is lower.Polyester resin of the present invention is in the extinction type powdery paints of HAA system
When, the film of available glossiness < 15%, and achieve excellent comprehensive performance.And commercially available common HAA polyester resin
Although abundant film-forming may be implemented, lower glossiness (comparative example 9) can not be obtained, the system delustring is unable to satisfy
Application requirement.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. a kind of HAA system extinction type polyester resin, which is characterized in that in terms of the total amount of the polyester resin, preparation is former
Material includes the raw material components of following molar percentage:
2. HAA system extinction type polyester resin according to claim 1, which is characterized in that with the polyester resin
Total amount meter prepares the raw material components that raw material includes following molar percentage:
3. HAA system extinction type polyester resin according to claim 1 or 2, which is characterized in that it further include catalyst,
The mole dosage of the catalyst accounts for the 0.1-0.3% of the raw material components integral molar quantity.
4. HAA system extinction type polyester resin according to claim 3, which is characterized in that the catalyst includes two
Lauric acid dioctyltin.
5. HAA system extinction type polyester resin according to claim 1-4, which is characterized in that further include resisting
Oxygen agent, the mole dosage of the antioxidant account for the 0.3-0.5% of the raw material components integral molar quantity.
6. HAA system extinction type polyester resin according to claim 5, which is characterized in that the antioxidant includes anti-
Oxygen agent 702.
7. a kind of method for preparing HAA system extinction type polyester resin described in any one of claims 1-6, feature exist
In including the following steps:
(1) a selected amount of 2- amino -4,6- dihydroxy-pyrimidine, neopentyl glycol, 1,10- decanediol, diacetone-D- sweet dew are taken
Sugar alcohol mixing, and temperature is controlled lower than 135 DEG C of progress heating meltings；
(2) a selected amount of terephthalic acid (TPA) and tetrahydrophthalic acid are added in Xiang Shangshu mixed material, and is added selected
The catalyst of amount is warming up to 200-210 DEG C of progress insulation reaction under nitrogen protection；Then gradually it is warming up to without obvious distillate
It steams, and the acid value of reactant is less than until 25mgKOH/g；
(3) a selected amount of antioxidant is added, keeps the vacuum degree 2-8h of 40-60mmHg, facilitates the formation of polyester resin, to acid value
Stop pulling vacuum when being reduced to 15mgKOH/g or less；
(4) when material being cooled to 200-210 DEG C, and a selected amount of Isosorbide-5-Nitrae is added, between 5,8- naphthalenetetracarbacidic acidic acid anhydrides, 5- methyl
Phthalic acid and Trimethyl citrate, and be to slowly warm up to 240 DEG C and end capping reaction 3-9h is carried out to polyester resin, the acid to reactant
Stop reaction when value is 26-34mgKOH/g, then material cools to 200 DEG C, and high temperature discharging while hot, through cooling, breaks
It is broken, be granulated to get.
8. the method for HAA system extinction type polyester resin described in preparation according to claim 8, which is characterized in that
In the step (2), the heating step is to be rapidly heated in 2h to 200-210 DEG C.
9. the purposes that HAA system described in any one of claims 1-6 is used to prepare powdery paints with extinction type polyester resin.
10. purposes according to claim 9, which is characterized in that the powdery paints is HAA system polyester powder coating.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810753591.8A CN110483751A (en) | 2018-07-10 | 2018-07-10 | A kind of HAA system extinction type polyester resin and the preparation method and application thereof |
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| CN201810753591.8A CN110483751A (en) | 2018-07-10 | 2018-07-10 | A kind of HAA system extinction type polyester resin and the preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111777925A (en) * | 2020-07-13 | 2020-10-16 | 安徽省华安进出口有限公司 | HAA system extinction powder coating |
| CN115505112A (en) * | 2022-10-26 | 2022-12-23 | 安徽永利新材料科技有限公司 | Low-cost and low-gloss polyester resin for powder coating and preparation method thereof |
-
2018
- 2018-07-10 CN CN201810753591.8A patent/CN110483751A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111777925A (en) * | 2020-07-13 | 2020-10-16 | 安徽省华安进出口有限公司 | HAA system extinction powder coating |
| CN115505112A (en) * | 2022-10-26 | 2022-12-23 | 安徽永利新材料科技有限公司 | Low-cost and low-gloss polyester resin for powder coating and preparation method thereof |
| CN115505112B (en) * | 2022-10-26 | 2023-09-19 | 安徽永利新材料科技有限公司 | Low-cost low-light type polyester resin for powder coating and preparation method thereof |
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