CN107778466B - A kind of HAA solidification thermal transfer type polyester resin for powder coating and preparation method thereof - Google Patents
A kind of HAA solidification thermal transfer type polyester resin for powder coating and preparation method thereof Download PDFInfo
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- CN107778466B CN107778466B CN201711036841.8A CN201711036841A CN107778466B CN 107778466 B CN107778466 B CN 107778466B CN 201711036841 A CN201711036841 A CN 201711036841A CN 107778466 B CN107778466 B CN 107778466B
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- polyester resin
- thermal transfer
- haa
- powder coating
- transfer type
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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
- C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
- C08G63/6954—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon derived from polxycarboxylic acids and polyhydroxy compounds
- C08G63/6956—Dicarboxylic acids and dihydroxy compounds
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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
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- 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
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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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
- C09D5/033—Powdery paints characterised by the additives
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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)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention discloses a kind of HAA to solidify thermal transfer type polyester resin for powder coating, the acid value of the polyester resin is 40~55mgKOH/g, 200 DEG C of melt viscosities are 2000~3500mPa.s, glass transition temperature is 55~65 DEG C, 180 DEG C of reactivity are 180~350s, are mainly obtained by the monomer component of following mass percentage by melt polycondensation reaction: dihydric alcohol: 24%~40% polyalcohol: 0.1%~0.5% end hydroxyl silicone oil: 0%~15% binary acid: 47%~58% acidolysis agent: 8%~12% catalyst: 0.01%~0.2%.The polyester resin has shorter curing time, and the powdery paints coating of preparation has good transferring effect, while having good levelability and excellent mechanical performance etc..Also disclose the preparation method that above-mentioned HAA solidifies thermal transfer type polyester resin for powder coating.
Description
Technical field
The invention belongs to polyester resin technical fields, and in particular to a kind of HAA solidification thermal transfer type powdery paints polyester
Resin and preparation method thereof.
Background technique
Thermal transfer is also referred to as heat sublimation, is to be printed on various patterns on high-precision paper using transfer ink, and turned using heat
Printing apparatus is heated to set temperature in a short time, is transferred to the pattern on transfer paper in the materials such as aluminum profile coating
A kind of special process.The technology is capable of providing bright in luster, and level transfer pattern abundant reaches the purpose of imitation wood line, stone image,
The use of a large amount of non-renewable natural resources can be saved, therefore is well received by the public from after occurring, market increases quick.City at present
The thermal transfer type powder coating resin overwhelming majority present on belongs to TGIC (isocyanuric acid three-glycidyl ester) type, due to
TGIC curing agent has certain toxicity all the time, since the nineties in last century, in the world many countries forbid in succession or
The application to it is limited, TGIC was also included in obsolete product catalogue in 2010 by Ministry of Industry and Information, China, therefore was developed a non-
The thermal transfer polyester resin for powder coating of TGIC system has been trend of the times.In numerous TGIC substitute products, HAA (hydroxyl alkane
Base amide) system curing agent is using one kind the most universal, product comprehensive performance is close to TGIC cured article and more
Environment-friendly advantage.There is different chemical structures, reactivity and curing mechanism since TGIC solidifies curing agent used from HAA,
There are Different Effects for the performance of coating, using TGIC type polyester resin carry out HAA solidification can exist difficult paper-tear picture, mimeograph it is more,
The problem of levelling, heat-resisting etc., it is difficult to general.
CN102977346A discloses a kind of TGIC and solidifies weather-proof thermal transfer polyester resin for powder coating and its preparation
Method provides a kind of glass transition temperature with higher, softening point, suitable melt viscosity and storage stability
Polyester resin has excellent thermal transfer effect by the powdery paints that the polyester resin is made, and the pattern lines after transfer is clear,
Not viscous transfer paper, paper-tear picture are easy.But when being solidified the resin using HAA and be prepared into powder coating, sticky paper after transfer is unable to reach
Requirement.
Currently, be mainly on the market polyester/TGIC system for thermal transfer type powdery paints, polyurethane system and poly-
Ester/epoxy type has no article and patent report for polyester/HAA system thermal transfer type polyester resin for powder coating.
Summary of the invention
The purpose of the present invention is to provide a kind of HAA to solidify thermal transfer type polyester resin for powder coating, the polyester resin
With shorter curing time, the powdery paints coating of preparation has good transferring effect, while having good levelability
And excellent mechanical performance etc..
The object of the invention is also to provide the preparation sides that above-mentioned HAA solidifies thermal transfer type polyester resin for powder coating
Method, the preparation method concise in technology are at low cost.
The first purpose of this invention is achieved through the following technical solutions: a kind of HAA solidification thermal transfer type powder
Coating polyester resin, the acid value of the polyester resin are 40~55mgKOH/g, 200 DEG C of melt viscosities are 2000~
3500mPa.s, glass transition temperature are 55~65 DEG C, and 180 DEG C of reactivity are 180~350s, mainly by following quality hundred
The monomer component of point content is obtained by melt polycondensation reaction:
Dihydric alcohol: 24%~40%
Polyalcohol: 0.1%~0.5%
End hydroxyl silicone oil: 0%~15%
Binary acid: 47%~58%
Acidolysis agent: 8%~12%
Catalyst: 0.01%~0.2%.
In each monomer component that above-mentioned HAA solidifies thermal transfer type polyester resin for powder coating:
Dihydric alcohol of the present invention is preferably the mixing of one or more of neopentyl glycol, ethylene glycol and diethylene glycol
Object.
Polyalcohol of the present invention is preferably trihydroxy methyl propane and/or monopentaerythritol.
End hydroxyl silicone oil of the present invention is preferably dimethyl silicone polymer and/or phenyl silicone.
Binary acid of the present invention is preferably one of terephthalic acid (TPA), M-phthalic acid, succinic acid and adipic acid
Or several mixture.
Acidolysis agent of the present invention is preferably one of M-phthalic acid, trimellitic anhydride and pyromellitic dianhydride or several
The mixture of kind.
Catalyst of the present invention is preferably organic tin.
Organic tin of the present invention is preferably Mono-n-butyltin.
Dihydric alcohol, polyalcohol, binary acid, end hydroxyl silicone oil, acidolysis agent in monomer component of the present invention are polyester tree
The skeleton structure component part of rouge, wherein acidolysis agent are also used as end-capping reagent；The catalyst is for accelerating synthetic reaction rate.
Above-mentioned second purpose of the invention is achieved through the following technical solutions: above-mentioned HAA solidifies thermal transfer type
The preparation method of polyester resin for powder coating, comprising the following steps:
(1) above-mentioned dosage relation is pressed, dihydric alcohol, polyalcohol and end hydroxyl silicone oil, heat temperature raising are added in the reaction vessel
Melt to material, then sequentially add binary acid and catalyst, open nitrogen protection and simultaneously gradually start to warm up, when being warming up to 220
~250 DEG C of (more preferably 240 DEG C) Shi Jinhang insulation reactions react the esterification of 10~13h to 85%~98% (more preferably to 95%)
After water discharge, acid value reaches 8~12mgKOH/g；
(2) it is subsequently added into acidolysis agent, reacts 2~4h, acid value reaches 50~70mgKOH/g, then vacuumizes 2~4h of polycondensation,
Acid value reaches 40~55mgKOH/g, 200 DEG C of 2000~3500mPa.s of melt viscosity, stops reaction and obtains HAA solidification thermal transfer
Type polyester resin for powder coating.
Compared with prior art, the present invention has the advantage that
(1) HAA curing agent is used, which has shorter curing time, and transfer paper-tear picture effect can reach or surpass
Cross polyester/TGIC system currently on the market；
(2) there is good levelability and excellent mechanical performance etc. using the powdery paints coating of above-mentioned resin preparation.
Detailed description of the invention
Fig. 1 is the thermal transfer effect picture of the embodiment of the present invention Yu comparative example paint coatings.
Specific embodiment
Following embodiment is used merely to explain the present invention, is not intended to limit protection scope of the present invention.The art it is common
The purpose of the present invention can be achieved according to range disclosed above in technical staff.
Below with reference to examples illustrate the present invention, table 1 is the embodiment of polyester resin.
Preparation method of polyester resin: being added dihydric alcohol, polyalcohol and end hydroxyl silicone oil into reaction kettle according to the ratio, and heating rises
Temperature to material melts, and then sequentially adds the binary acid and catalyst of proportional quantity, opens nitrogen protection and gradually starts to warm up, when
Insulation reaction is carried out when being warming up to 220~250 DEG C, after the esterification water discharge of reaction 10~13 hours to 85%~98%, acid value
Reach 8~12mgKOH/g；Acidolysis agent is added, reacts 2~4 hours, acid value reaches 50~70mgKOH/g, vacuumizes polycondensation 2~4
Hour, acid value reaches 40~55mgKOH/g, 200 DEG C of 2000~3500mPa.s of melt viscosity, stops reaction and obtains HAA solidification heat
Transfer printing type polyester resin for powder coating.
The component and performance of 1 polyester resin of table
It will be applied on powdery paints respectively according to polyester resin made from Examples 1 to 5 method, the process has tree
Rouge is uniformly mixed with curing agent HAA, titanium dioxide, barium sulfate, levelling agent, styrax and brightener by formula rate, passes through double spiral shells
The tabletting of bar extruder, cooling broken, sieving and electrostatic spraying.
The composition and coating performance of 2 powdery paints of table
As shown in Table 2, have when being transferred using polyester resin prepared by formula of the invention and technique for powder coating
Good effect, while there is good levelability and excellent mechanical performance.In addition, using matching in comparative example 1 and comparative example 2
There is sticky paper phenomenon in transfer in the powder coating of square polyester resin preparation, and transferring effect is poor.
Resin in embodiment 1, embodiment 4, comparative example 1 and comparative example 2 is prepared into powder according to powder coating formulation respectively
Last coating, carries out thermal transfer experiment under the conditions of identical transfer, and transferring effect figure is as shown in Figure 1.
Each component cited by the present invention, and bound, the section value of each component of the present invention can realize the present invention,
Embodiment numerous to list herein.A part of specific embodiment is enumerated above, and the present invention will be described, it is necessary to it is pointed out here that
Be that specific embodiment is served only for that the present invention is further illustrated up and down, do not represent limiting the scope of the invention.
The some nonessential modifications and adjustment that other people make according to the present invention still fall within protection scope of the present invention.
Claims (9)
1. a kind of HAA solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: the acid value of the polyester resin be 40~
55mgKOH/g, 200 DEG C of melt viscosities are 2000~3500mPa.s, and glass transition temperature is 55~65 DEG C, 180 DEG C of reactivity
For 180~350s, mainly obtained by the monomer component of following mass percentage by melt polycondensation reaction:
Dihydric alcohol: 24%~40%
Polyalcohol: 0.1%~0.5%
End hydroxyl silicone oil: 0%~15%
Binary acid: 47%~58%
Acidolysis agent: 8%~12%
Catalyst: 0.01%~0.2%.
2. HAA according to claim 1 solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: described two
First alcohol is the mixture of one or more of neopentyl glycol, ethylene glycol and diethylene glycol.
3. HAA according to claim 1 solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: described is more
First alcohol is trihydroxy methyl propane and/or monopentaerythritol.
4. HAA according to claim 1 solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: the end
Hydroxy silicon oil is dimethyl silicone polymer and/or phenyl silicone.
5. HAA according to claim 1 solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: described two
First acid is the mixture of one or more of terephthalic acid (TPA), M-phthalic acid, succinic acid and adipic acid.
6. HAA according to claim 1 solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: the acid
Solution agent is the mixture of one or more of M-phthalic acid, trimellitic anhydride and pyromellitic dianhydride.
7. HAA according to claim 1 solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: described urges
Agent is organic tin.
8. HAA according to claim 7 solidifies thermal transfer type polyester resin for powder coating, it is characterized in that: described has
Machine tin class is Mono-n-butyltin.
9. the described in any item HAA of claim 1-8 solidify the preparation method of thermal transfer type polyester resin for powder coating, special
Sign be the following steps are included:
(1) above-mentioned dosage relation is pressed, dihydric alcohol, polyalcohol and end hydroxyl silicone oil are added in the reaction vessel, is heated to object
Material melts, and then sequentially adds binary acid and catalyst, opens nitrogen protection and simultaneously gradually starts to warm up, when being warming up to 220~250
DEG C when carry out insulation reaction, after the esterification water discharge of reaction 10~13h to 85%~98%, acid value reaches 8~12mgKOH/g；
(2) it is subsequently added into acidolysis agent, reacts 2~4h, acid value reaches 50~70mgKOH/g, then vacuumizes 2~4h of polycondensation, acid value
Reach 40~55mgKOH/g, 200 DEG C of 2000~3500mPa.s of melt viscosity, stops reaction and obtain HAA solidification thermal transfer type powder
Last coating polyester resin.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711036841.8A CN107778466B (en) | 2017-10-30 | 2017-10-30 | A kind of HAA solidification thermal transfer type polyester resin for powder coating and preparation method thereof |
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| CN201711036841.8A CN107778466B (en) | 2017-10-30 | 2017-10-30 | A kind of HAA solidification thermal transfer type polyester resin for powder coating and preparation method thereof |
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| CN107778466B true CN107778466B (en) | 2019-11-19 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109762145A (en) * | 2018-11-30 | 2019-05-17 | 安徽神剑新材料股份有限公司 | A kind of hydroxyalkyl amide solidification thermal transfer powdery paints carboxyl end group saturated polyester resin and its synthetic method |
| CN109734882A (en) * | 2018-11-30 | 2019-05-10 | 安徽神剑新材料股份有限公司 | A kind of three-glycidyl isocyanurate curing thermal transfer powdery paints carboxyl end group saturated polyester resin and its synthetic method |
| CN110527412A (en) * | 2019-10-22 | 2019-12-03 | 广西南宁维一防腐科技有限公司 | A kind of solidification thermal transfer powder of environmental protection and preparation method thereof |
| CN110790909B (en) * | 2019-10-30 | 2022-03-15 | 擎天材料科技有限公司 | Polyester resin and preparation method thereof |
| CN114181384B (en) * | 2021-12-20 | 2023-04-18 | 黄山市徽州康佳化工有限责任公司 | Polyester resin for low-cost, pinhole-resistant and high-hardness HAA system and preparation method thereof |
| CN116804081B (en) * | 2023-08-01 | 2024-01-23 | 安徽永昌新材料有限公司 | Silicon-based curing type polyester resin, preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101985538A (en) * | 2010-10-27 | 2011-03-16 | 中国电器科学研究院 | Environment-friendly low-temperature curing pure polyester powder paint and preparation method thereof |
| CN105218795A (en) * | 2015-10-22 | 2016-01-06 | 广州擎天材料科技有限公司 | A kind of HAA solidifies coiled material pure polyester resin used for powder coating and preparation method thereof |
| CN106543418A (en) * | 2016-10-24 | 2017-03-29 | 广州擎天材料科技有限公司 | A kind of grit powder coating polyester resin of HAA solidifications and preparation method thereof |
| CN106750207A (en) * | 2016-11-04 | 2017-05-31 | 广州擎天材料科技有限公司 | High acid value amorphous polyester resin and preparation method and the solidifications of the HAA comprising the polyester resin once extrude low brightness paint powder |
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2017
- 2017-10-30 CN CN201711036841.8A patent/CN107778466B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101985538A (en) * | 2010-10-27 | 2011-03-16 | 中国电器科学研究院 | Environment-friendly low-temperature curing pure polyester powder paint and preparation method thereof |
| CN105218795A (en) * | 2015-10-22 | 2016-01-06 | 广州擎天材料科技有限公司 | A kind of HAA solidifies coiled material pure polyester resin used for powder coating and preparation method thereof |
| CN106543418A (en) * | 2016-10-24 | 2017-03-29 | 广州擎天材料科技有限公司 | A kind of grit powder coating polyester resin of HAA solidifications and preparation method thereof |
| CN106750207A (en) * | 2016-11-04 | 2017-05-31 | 广州擎天材料科技有限公司 | High acid value amorphous polyester resin and preparation method and the solidifications of the HAA comprising the polyester resin once extrude low brightness paint powder |
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Address after: No.5 Lisha East Road, Shatian Town, Dongguan City, Guangdong Province 523000 Patentee after: Qingtian Material Technology Co., Ltd Address before: Shiling Town, Huadu District, Guangzhou City, Guangdong province 510860 Yufeng Road No. 16 Patentee before: GUANGZHOU KINTE INDUSTRIAL Co.,Ltd. |
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