CN105367765A - Polyester resin used for TGIC curing high-toughness thermal transfer printing powder paints, and preparation method thereof - Google Patents
Polyester resin used for TGIC curing high-toughness thermal transfer printing powder paints, and preparation method thereof Download PDFInfo
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- CN105367765A CN105367765A CN201510895524.6A CN201510895524A CN105367765A CN 105367765 A CN105367765 A CN 105367765A CN 201510895524 A CN201510895524 A CN 201510895524A CN 105367765 A CN105367765 A CN 105367765A
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Abstract
The invention relates to a polyester resin used for TGIC curing high-toughness thermal transfer printing powder paints, and a preparation method thereof. The glass-transition temperature of the polyester resin is relatively high, so that prepared powder paint coating possesses high toughness at normal temperature and -15 DEG C. According to the preparation method, the polyester resin is obtained via melt polycondensation of following raw materials: a polyol, a polyacid, an acidolysis agent, an esterification catalyst, an antioxidant, and a curing accelerator. The preparation method comprises following steps: 1) the polyol is delivered into a reaction kettle at a needed ratio, rapid heating esterification is carried out, water is generated, and is removed via distillation; 2) temperature is increased gradually, and an obtained material is maintained to be clear; 3) sample examination is carried out; 4) one half of the antioxidant is added, and negative pressure polycondensation is carried out; and 5) cooling is carried out, one half of the antioxidant and the curing accelerator are added, stirring dispersing is carried out, and an obtained product is cooled, and is collected.
Description
Technical field
The present invention relates to a kind of vibrin, particularly relate to triglycidyl isocyanurate (TGIC) and solidify high-toughness hot transfer printing polyester resin for powder coating, the invention still further relates to the preparation method of this polyester.
Technical background
Powder coating is that a kind of solvent-free environmental protection class coating is applied widely in the field such as building materials and house ornamentation, possesses the advantages such as preparation is simple, efficient, the economic environmental protection of application, superior performance.The composition of powder coating is formed primarily of matrix resin, solidifying agent, color stuffing and auxiliary agent.Vibrin is the one in matrix resin used for powder coating, is the macromolecule prepolymer obtained through melt polymerization by polyprotonic acid and polyvalent alcohol.For powder coating systems, require that vibrin possesses higher second-order transition temperature (40 ~ 70 DEG C) and certain active function groups and functionality.
The performance of cured coating film depends primarily on the vibrin performance as main film forming substance, comprehensive mechanical performance (shock-resistance and resistance to bending) investigates the important indicator one of of polymer composite for base protection reliability, good comprehensive mechanical performance can improve film to the protective of base material and weather resistance, can improve secondary workability simultaneously; Because the mobility of polymeric segment declines with the reduction of temperature, so the mechanical property of cured coating film can decline along with environment for use temperature and reduce.Synthesis and preparative for high flexibility vibrin also has some to report before this, it is monomer modified with long-chain fat race in vibrin synthesizing formula for being coated with film toughness main method for lifting in the industry, high tenacity polyester resin for powder coating is solidified as Chinese patent CN103739830A discloses a kind of TGIC, a large amount of hexanodioic acids introduced by this polyester, SA, the long-chain fat race monomers such as nonane diacid, can infer that this resin possesses outstanding snappiness, but a large amount of second-order transition temperature using long-chain fat race monomer can reduce vibrin, affect powder coating stability in storage.
Hot transfer printing is also referred to as heat sublimation, by arbitrary graphics such as portrait, landscape, wood grain, marble grain, plastic reliefs, hot transfer ink is used to be imprinted on high precision paper, pass through corresponding hot transfer apparatus again, be heated to certain temperature at short notice, the image on paper, color, be transferred to a kind of special process in the materials such as aluminium section bar realistically.Hot transfer printing is the technique means of improvement decorative coating film performance fast-developing in recent years, has the advantages such as efficient, economic, stable and pattern is abundant.Therefore develop rapidly as new decorative means in powder coating in recent years.Synthesis and preparative for transfer printing polyester resin for powder coating also has some report industry before this, in the industry for the way improving adhering molding transfer performance, is with a large amount of rigid unitary modification in vibrin building-up process; Chinese patent CN102977346A discloses a kind of TGIC and solidifies the hot transfer printing polyester resin for powder coating of weather resistant, this vibrin uses a large amount of neopentyl glycol, therefore can infer that film coated surface hardness prepared by this vibrin is higher, but the transfer printing film mechanical property prepared by this vibrin is general.
Summary of the invention
The object of this invention is to provide a kind of TGIC and solidify high tenacity, hot transfer printing polyester resin for powder coating, this vibrin has higher second-order transition temperature, the powder coating film of preparation all possesses high tenacity normal temperature and-15 DEG C, the powder coating simultaneously prepared possesses higher cross-linking density, after hot transfer printing, film pattern texture is clear, not sticky paper.
Another object of the present invention is to provide the preparation method that a kind of TGIC solidifies high tenacity, hot transfer printing polyester resin for powder coating.
First object of the present invention is achieved through the following technical solutions:
A kind of TGIC solidifies high tenacity, hot transfer printing polyester resin for powder coating, acid number is 38.0 ~ 46.0mgKOH/g, hydroxyl value is less than 6.0mgKOH/g, second-order transition temperature is 64.0 ~ 70.0 DEG C, rotation viscosity is 3000 ~ 6000CPas (200 DEG C), number-average molecular weight is 2000 ~ 6000, is obtained through melt polycondensation reaction by the raw material of following weight part:
Polyvalent alcohol: 25.0 ~ 45.0
Polyprotonic acid: 45.0 ~ 55.0
Acidolysis agent: 6.0 ~ 12.0
Esterifying catalyst: 0.03 ~ 0.12
Oxidation inhibitor: 0.4 ~ 1.2
Curing catalyst: 0.02 ~ 0.4
Described polyvalent alcohol comprises neopentyl glycol and 2-methyl isophthalic acid, 3 propylene glycol, also comprises TriMethylolPropane(TMP) or Isosorbide-5-Nitrae-cyclohexane dimethyl carbinol; It is any part by weight between each component;
Described polyprotonic acid comprises hexanodioic acid and terephthalic acid, also comprises one or more mixtures in m-phthalic acid, NDA, 1,2,4-benzene tricarboxylic acid acid anhydride and Isosorbide-5-Nitrae-cyclohexane dioctyl phthalate; It is any part by weight between each component;
Described acidolysis agent is the mixture of one or both any part by weight in m-phthalic acid and 1,2,4-benzene tricarboxylic acid acid anhydride;
Described esterifying catalyst is the mixture of one or both any part by weight in Mono-n-butyltin and Dibutyltin oxide;
Described oxidation inhibitor is the mixture of one or both any part by weight in Hinered phenols antioxidant and phosphite ester kind antioxidant; Hinered phenols antioxidant is four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, and phosphite ester kind antioxidant is tricresyl phosphite (2.4-di-tert-butyl-phenyl) ester.
Described curing catalyst is tri-phenyl-phosphorus bromide, comprises the one in methyltriphenylphospbromide bromide phosphorus, Ethyltriphenylphosphonium brimide, isopropyl triphenyl bromo-phosphonium.
Second object of the present invention is realized by following technical scheme:
TGIC solidifies a preparation method for high tenacity, hot transfer printing polyester resin for powder coating, carries out according to following steps:
1) in a kettle., add required polyvalent alcohol by proportioning, polyprotonic acid and esterifying catalyst, under nitrogen atmosphere protection, be rapidly heated to 160 ~ 180 DEG C of esterification water and generate and distillate;
2) be then progressively warming up to 250 DEG C with the speed of 8 ~ 10 DEG C/h, remain on 250 DEG C of reaction to materials and clarify;
3) sampling detects, and after acid number reaches 12-18mgKOH/g, adds acidolysis agent by proportioning, reacts 1 ~ 3 hour;
4) acid number reaches 47 ~ 54mgKOH/g, adds 1/2nd oxidation inhibitor, 0.0113 ~ 0.0093MPa negative pressure polycondensation 1 ~ 3 hour;
5) when acid number reaches 38.0 ~ 46.0mgKOH/g, be cooled to 230 DEG C, add 1/2nd oxidation inhibitor and curing catalyst, after dispersed with stirring, namely cooling discharge obtains TGIC solidification high-toughness hot transfer printing polyester resin for powder coating.
Described step 2) in need to record the weight of esterification water, when esterification water aquifer yield reaches 95% of theoretical value.Sampling detects acid number.
Polyester prepared by the inventive method is unformed terminal carboxyl polyester resin, acid number is 38.0 ~ 46.0mgKOH/g, and hydroxyl value is less than 6.0mgKOH/g, and second-order transition temperature is 64.0 ~ 70.0 DEG C, rotation viscosity is 3000 ~ 6000CPas (200 DEG C), and number-average molecular weight is 2000 ~ 6000.Polyester prepared by the inventive method has higher second-order transition temperature, the powder coating of preparation, all possess outstanding toughness normal temperature and-15 DEG C, the powder coating simultaneously prepared possesses higher cross-linking density, after hot transfer printing, film pattern texture is clear, not sticky paper.
The vibrin of the present invention's synthesis is adopted to prepare the step of hot transfer printing powder coating, be by synthesis vibrin respectively with solidifying agent TGIC (isocyanuric acid three-glycidyl ester), filler, pigment and other auxiliary agent are prepared burden in proportion, even through physical mixed, melt extrude, cooling is broken, coating can (color stuffing comprises titanium dioxide to grinding sieve series powdered, barium sulfate, chrome yellow, carbon black etc., other auxiliary agent comprises st-yrax, flow agent, texture agent etc.), then with electrostatic gun by powder paint to campstool steel plate, 200 DEG C/15min takes out after solidifying, after cooling, transfer paper is wrapped in specimen surface, take out after flat transfer machine 200 DEG C/2min heats, after taking out cooling, paper-tear picture can obtain the figuratum film of tool.
The invention has the beneficial effects as follows:
A. 2 are adopted in the polyester formulation that prepared by the present invention, 6-naphthalic acid, compared with conventional aromatic acid (terephthalic acid, m-phthalic acid) monomer, 2, in 6-naphthalene diacid, naphthalene nucleus has that steric hindrance is large and rigidity is strong, the second-order transition temperature of vibrin can be improved, significantly improve the problem of the vibrin second-order transition temperature decline that long-chain fat race monomer causes, promote the stability in storage of the powder coating prepared by this vibrin.
B. 1 is adopted in the present invention's formula, 4-cyclohexanedimethanol and 1, the monomers such as 4-cyclohexane cyclohexanedimethanodibasic, the boat form that such monomer contains and chair form six circular ring structure, such monomer access vibrin molecular backbone chain, the film of preparation in use relies on vibrin Conformation of the main chain to change absorption energy, thus improve the problem postponing impact property and decline, six circular ring structures and long-chain fat race monomer produce and act synergistically simultaneously, make film have outstanding toughness, also possess outstanding mechanical property at low temperatures.
C. the vibrin acid number that prepared by the present invention is 38.0 ~ 46.0mgKOH/g, compared with conventional polyester resin, vibrin exposed terminated groups functional group provided by the invention is more and functionality is larger, the powder coating cross-linking density of preparation is high, compact structure after curing of coating, surface hardness is high, and hot transfer pressure process window is large, transfer printing is clear, not easily sticky paper.Therefore the vibrin that prepared by the present invention at low temperatures for base material provides outstanding protective value, can be applicable to caloric transfer printing technology simultaneously, possesses outstanding decorate properties, be applicable to extreme low temperature applied environment.
Accompanying drawing explanation
Fig. 1 to Fig. 4 is the hot transferring effect figure of the embodiment of the present invention.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but following embodiment is just for setting forth content of the present invention, instead of restriction, therefore any change in the implication suitable with claims of the present invention and scope, all should think to be included in the scope of claims.
Table 1 is the embodiment of vibrin, and wherein embodiment a is the basic with reference to comparative formula of vibrin, and as comparative example of the present invention, embodiment b--f is 5 embodiments of the present invention; The preparation method of these embodiments, is all in the reactor of 3000ml, adds the polyvalent alcohol of proportional quantity listed by table 1, polyprotonic acid and esterifying catalyst; Under nitrogen atmosphere protection, be rapidly heated to 160 ~ 180 DEG C of esterification water and generate and distillate, be then progressively warming up to 250 DEG C with the speed of 8 ~ 10 DEG C/h, remain on 250 DEG C of reaction to materials and clarify; The weight of record esterification water, when esterification water aquifer yield reaches 95% of theoretical value, sampling detects acid number; After acid number reaches acceptability limit, add acidolysis agent by proportioning, react 1 ~ 3 hour, sampling detects acid number; After acid number reaches acceptability limit, add oxidation inhibitor, then carry out negative pressure (-0.090 ~-0.092MPa) polycondensation, react 1 ~ 3 hour, sampling detecting acid number; After acid number reaches acceptability limit, be cooled to 230 DEG C, add oxidation inhibitor and curing catalyst; After dispersed with stirring, cooling discharge, namely obtains TGIC and solidifies high-toughness hot transfer printing polyester resin for powder coating.Acid number is 38.0 ~ 46.0mgKOH/g, and hydroxyl value is less than 6.0mgKOH/g, and second-order transition temperature is 64.0 ~ 70.0 DEG C, and rotation viscosity is 3000 ~ 6000CPas (200 DEG C), and number-average molecular weight is 2000 ~ 6000.
The component of table 1 vibrin and performance
Note: the acid number of resin tests the standard detection according to GB/T6743-2008
The melting rotary viscosity of resin tests the standard detection according to GB/T9751.1-2008
The second-order transition temperature of resin measures the standard detection according to GB/T19466.2-2004
The softening point measurement of resin is according to the standard detection of GB/T27808-2011
The determination of colority of resin is according to the standard detection of GB/T9282.1-2008
Performance and the hot transferring effect of the vibrin of the present invention's synthesis are embodied by the performance of the powder coating be made into.Mix after the vibrin of the embodiment a in the present invention ~ embodiment f is weighed up in the ratio in table 2 with TGIC, flow agent, titanium dioxide, barium sulfate, st-yrax and brightening agent (701) etc. respectively, extrude respectively with screw extrusion press melting, compressing tablet, fragmentation, sieve series powdered coating.With electrostatic gun by powder paint on the metal sheet crossed through alramenting, solidify through 200 DEG C/15min, then by heat transfer machine 200 DEG C/2min heating transfer, paper is torn after cooling, carrying out properties test, the performance test results is as shown in table 2, and hot transferring effect is shown in Fig. 1.
The composition of table 2 powder coating and film performance
Note:
1. solidifying agent TGIC: isocyanuric acid three-glycidyl ester (Changzhou Niu Tang Chemical Co., Ltd.), equivalent: 108g/mol
2.GLP588: the special flow agent of powder coating (the polyacrylate(s) flow agent that Ningbo South-sea Chemical Co., Ltd. produces)
3.BLC701701: optical brightener used for powder coating (acrylate copolymer that ripple South Sea Chemical Co., Ltd. produces is the powder coating additive of main body)
4, titanium dioxide r902: pigment used for powder coating (du pont company)
5, process white W5HB: filler used for powder coating (Shaanxi enrichment company)
6, st-yrax: air release agent used for powder coating
7. the resin a ~ resin f in table is the resin that the embodiment a ~ embodiment f in table 1 obtains successively; Example adopts above-mentioned resin to add the powder coating that auxiliary material is obtained.
8. powder coating film performance testing standard
The thickness measuring of film is according to the standard detection of GB/T13452.2-2008
The measurement of luster of film is according to the standard detection of GB/T1743-1979
The standard detection according to GB23989-2009 is tested in the solvent resistant wiping of film
The impact property of film tests the standard detection according to GB-T1732-1993
The flexility of film tests the standard detection according to GB/T1731-1993
By table 1 ~ 2 and Fig. 1 ~ 4 known, vibrin prepared by the inventive method has higher second-order transition temperature, by the standby powder coating film of this resin-made at normal temperatures and about-15 DEG C have excellent toughness, hot good transferring effect, clear patterns, the features such as paper-tear picture is easy.Therefore the vibrin that prepared by the present invention at low temperatures for base material provides outstanding protective value, can be applicable to caloric transfer printing technology simultaneously, possesses outstanding decorate properties, be applicable to extreme low temperature applied environment.
Claims (6)
1. a TGIC solidifies high tenacity, hot transfer printing polyester resin for powder coating, acid number is 38.0 ~ 46.0mgKOH/g, hydroxyl value is less than 6.0mgKOH/g, second-order transition temperature is 64.0 ~ 70.0 DEG C, rotation viscosity is 3000 ~ 6000CPas (200 DEG C), number-average molecular weight is 2000 ~ 6000, is obtained through melt polycondensation reaction by the raw material of following weight part:
Polyvalent alcohol: 25.0 ~ 45.0
Polyprotonic acid: 45.0 ~ 55.0
Acidolysis agent: 6.0 ~ 12.0
Esterifying catalyst: 0.03 ~ 0.12
Oxidation inhibitor: 0.4 ~ 1.2
Curing catalyst: 0.02 ~ 0.4;
Described polyvalent alcohol comprises neopentyl glycol and 2-methyl isophthalic acid, 3 propylene glycol, also comprises TriMethylolPropane(TMP) or Isosorbide-5-Nitrae-cyclohexane dimethyl carbinol; It is any part by weight between each component;
Described polyprotonic acid comprises hexanodioic acid and terephthalic acid, also comprises one or more mixtures in m-phthalic acid, NDA and Isosorbide-5-Nitrae-cyclohexane dioctyl phthalate, 1,2,4-benzene tricarboxylic acid acid anhydride; It is any part by weight between each component;
Described acidolysis agent is the mixture of one or both any part by weight in m-phthalic acid and 1,2,4-benzene tricarboxylic acid acid anhydride.
2. TGIC according to claim 1 solidifies high tenacity, hot transfer printing polyester resin for powder coating, it is characterized in that described esterifying catalyst is the mixture of one or both any part by weight in Mono-n-butyltin and Dibutyltin oxide.
3. TGIC according to claim 2 solidifies high tenacity, hot transfer printing polyester resin for powder coating, it is characterized in that described oxidation inhibitor is the mixture of one or both any part by weight in Hinered phenols antioxidant and phosphite ester kind antioxidant; Hinered phenols antioxidant is four [β-(3,5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, and phosphite ester kind antioxidant is tricresyl phosphite (2.4-di-tert-butyl-phenyl) ester.
4. TGIC according to claim 3 solidifies high tenacity, hot transfer printing polyester resin for powder coating, it is characterized in that described curing catalyst is tri-phenyl-phosphorus bromide, comprise the one in methyltriphenylphospbromide bromide phosphorus, Ethyltriphenylphosphonium brimide, isopropyl triphenyl bromo-phosphonium.
5. TGIC according to claim 1 solidifies the preparation method of high tenacity, hot transfer printing polyester resin for powder coating, carries out according to following steps:
1) in a kettle., add required polyvalent alcohol by proportioning, polyprotonic acid and esterifying catalyst, under nitrogen atmosphere protection, be rapidly heated to 160 ~ 180 DEG C of esterification water and generate and distillate;
2) be then progressively warming up to 250 DEG C with the speed of 8 ~ 10 DEG C/h, remain on 250 DEG C of reaction to materials and clarify;
3) sampling detects, and after acid number reaches 12-18mgKOH/g, adds acidolysis agent by proportioning, reacts 1 ~ 3 hour;
4) acid number reaches 47 ~ 54mgKOH/g, adds 1/2nd oxidation inhibitor, 0.0113 ~ 0.0093MPa negative pressure polycondensation 1 ~ 3 hour;
5) when acid number reaches 38.0 ~ 46.0mgKOH/g, be cooled to 230 DEG C, add 1/2nd oxidation inhibitor and curing catalyst, after dispersed with stirring, namely cooling discharge obtains TGIC solidification high-toughness hot transfer printing polyester resin for powder coating.
6. TGIC according to claim 5 solidifies the preparation method of high tenacity, hot transfer printing polyester resin for powder coating, it is characterized in that described step 2) in need to record the weight of esterification water, when esterification water aquifer yield reaches 95% of theoretical value, sampling detects acid number.
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| CN106318143A (en) * | 2016-08-24 | 2017-01-11 | 六安科瑞达新型材料有限公司 | Wooden transfer power paint for aluminium profile |
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106318143A (en) * | 2016-08-24 | 2017-01-11 | 六安科瑞达新型材料有限公司 | Wooden transfer power paint for aluminium profile |
| CN106634476A (en) * | 2016-09-30 | 2017-05-10 | 浙江传化天松新材料有限公司 | Epoxy cured high-flexibility polyester resin used for powdery paint and a preparing method thereof |
| CN106634476B (en) * | 2016-09-30 | 2019-08-02 | 浙江传化天松新材料有限公司 | A kind of curable epoxide high-flexibility polyester resin for powder coating and preparation method thereof |
| CN106867371A (en) * | 2017-03-14 | 2017-06-20 | 广东华江粉末科技有限公司 | A kind of aluminium section bar counter-bending thermal transfer powdery paints of low gloss and preparation method thereof |
| CN106867371B (en) * | 2017-03-14 | 2020-03-20 | 广东华江粉末科技有限公司 | Low-gloss bending-resistant thermal transfer printing powder coating for aluminum profile and preparation method thereof |
| CN107254240B (en) * | 2017-04-20 | 2019-05-28 | 浙江传化天松新材料有限公司 | A kind of high decorative surface of curable epoxide, enhanced water resistance polyester resin for powder coating and preparation method thereof |
| CN107254240A (en) * | 2017-04-20 | 2017-10-17 | 浙江传化天松新材料有限公司 | A kind of high decorative surface of curable epoxide, enhanced water resistance polyester resin for powder coating and preparation method thereof |
| CN107619472A (en) * | 2017-08-16 | 2018-01-23 | 江苏宝田新型材料科技股份有限公司 | A kind of thermal transfer powdery paints outdoor pure polyester resin and preparation method thereof |
| TWI774922B (en) * | 2018-02-07 | 2022-08-21 | 南韓商Ｓｋ化學公司 | Saturated copolyester resin and coating composition comprising same |
| CN108795257A (en) * | 2018-06-05 | 2018-11-13 | 帝兴树脂(昆山)有限公司 | Low Tg polyester of a kind of cured superelevation levellings of TGIC and preparation method thereof |
| CN108795257B (en) * | 2018-06-05 | 2020-10-30 | 帝兴树脂(昆山)有限公司 | TGIC (triglycidyl isocyanurate) cured ultrahigh-leveling low-Tg polyester and preparation method thereof |
| CN111533892A (en) * | 2020-06-03 | 2020-08-14 | 浙江传化天松新材料有限公司 | Polyester resin for high-weather-resistance low-temperature TGIC (triglycidyl isocyanurate) curing powder coating and preparation method thereof |
| CN111533892B (en) * | 2020-06-03 | 2022-10-21 | 浙江传化天松新材料有限公司 | Polyester resin for high-weather-resistance low-temperature TGIC (triglycidyl isocyanurate) curing powder coating and preparation method thereof |
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| CN114133538A (en) * | 2021-12-13 | 2022-03-04 | 安徽美佳新材料股份有限公司 | Special polyester resin for anti-sticking hanger powder coating and preparation method thereof |
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