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CN109762145A - A kind of hydroxyalkyl amide solidification thermal transfer powdery paints carboxyl end group saturated polyester resin and its synthetic method - Google Patents

A kind of hydroxyalkyl amide solidification thermal transfer powdery paints carboxyl end group saturated polyester resin and its synthetic method Download PDF

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Publication number
CN109762145A
CN109762145A CN201811458610.0A CN201811458610A CN109762145A CN 109762145 A CN109762145 A CN 109762145A CN 201811458610 A CN201811458610 A CN 201811458610A CN 109762145 A CN109762145 A CN 109762145A
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polyester resin
thermal transfer
resin
end group
powdery paints
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翟春海
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Anhui Shenjian New Materials Co Ltd
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Anhui Shenjian New Materials Co Ltd
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Abstract

The present invention provides a kind of hydroxyalkyl amide solidification thermal transfer powdery paints carboxyl end group saturated polyester resin and its synthetic method, is mainly formed by the raw material melt polycondensation of following weight percent: polyalcohol: 30-45%wt;Aromatic polycarboxylic acid 43-55%wt;Branching agent: 0.01-3%wt;Acidolysis agent: 8-18%wt;Esterification catalyst 0.03-0.15%wt;Antioxidant 0.01-2%wt.With suitable glass transition temperature, storage stability and synthetic technology of resins is simple and the advantages such as resin is at low cost, resin component meets requirement about polyester resin for powder coating in " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: dust profile ", with HAA be used in conjunction made of coating after powder coating solidification there is levelling and that mechanical performance performance is good, weather resistance meets the II grade standard of " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: dust profile ", thermally transferred pattern is clear and without offset printing.

Description

A kind of hydroxyalkyl amide solidification thermal transfer powdery paints carboxyl end group saturated polyester resin And its synthetic method
Technical field
The present invention relates to art of powder coatings more particularly to a kind of hydroxyalkyl amide to solidify thermal transfer powdery paints end carboxylic Base saturated polyester resin and its synthetic method.
Background technique
At present the extensive application field of powdery paints first is that aluminum profile, latest national standards " GB/T 5237.4-2008 The 4th part of aluminum alloy building section: dust profile " a large amount of requirement is proposed to polyester resin for powder coating.Specifically such as Under: other not hydrogeneous polyalcohols also can be used usually based on neopentyl glycol in the polyalcohol of 1. synthesis polyester, it should be noted that The purity of polyalcohol.Neopentyl glycol is preferably produced with hydrogenation method, is disapproved using ethylene glycol, diethylene glycol, propylene glycol;Promote resin The mass fraction ratio of middle M-phthalic acid (or excellent weather resistance and hard is in other binary acid of M-phthalic acid) and terephthalic acid (TPA), benefit In raising powder weatherability.For guarantee powder film layer weatherability, M-phthalic acid (or excellent weather resistance and hard in M-phthalic acid its His binary acid) the suitable > 15% of mass fraction in resin, but encourage under the premise of improving weatherability, use the formula of innovation And process system.Also the weatherability of powdery paints is classified simultaneously, specific as follows: III level is that xenon lamp 4000h gloss retention is >=it be xenon lamp 1000h gloss retention in 75%, II grades be >=90%, I grades be xenon lamp 1000h gloss retention is >=50%.
Outdoor powdery paints conventional at present can satisfy I grade standard substantially, and meet the normal in the market of II grades of weathering protocols Rule weather-resistant powder paint does not have then substantially.In outdoor polyester resin normally be all added to a small amount of ethylene glycol etc. with reduce at This, while kind seldom in conventional weatherable polyether resin can satisfy M-phthalic acid content accounts for resin quality 15%, heat turns The ratio of M-phthalic acid station resin quality is also preferably below 12% in print polyester resin for powder coating.Therefore these kinds is poly- Ester resin is unable to satisfy new national standard, will finally be eliminated by aluminium profile market.
Since three-glycidyl chlorinated isocyanurates (TGIC) has certain physiological-toxicity, it is included at present by Ministry of Industry and Information It eliminates the backward production facilities, therefore developing one kind in the market to substitute the cured powdery paints of TGIC has been trend of the times, numerous In TGIC substitute products, hydroxyalkyl amide (HAA, product name T105) is current most popular one kind, and performance is close to TGIC Curing system and asepsis environment-protecting.It is different from TGIC, the functional group reacted in HAA system is hydroxyl, there is no effective catalysis at present Agent is catalyzed itself and polyester resin reaction, it is therefore desirable to which special exploitation is suitable for the polyester resin of hydroxyalkyl amide.It is conventional at present to answer There is a large amount of HAA cured polyester resin supply market with field, but it is commercialized in thermal transfer art of powder coatings Product does not have but.
CN107619472A discloses a kind of preparation method of thermal transfer powder coating resin, uses in raw material The component of PET causes to cause there is a large amount of beta hydrogen weatherability insufficient in system, is unable to satisfy " GB/T 5237.4- The 4th part of 2008 aluminum alloy building section: dust profile " requirement.CN105367765B discloses a kind of ultra-tough heat turn The preparation method of powder coating resin is printed, largely adds 2- methyl-1 in formula, 3 propylene glycol are with the tough of the system of adding Property, the whole weather resistance for being is relatively low.CN106893086A provides a kind of thermal transfer polyester resin for powder coating preparation side Method, wherein using a large amount of M-phthalic acid to improve its weather resistance.But early period, a large amount of acid-alcohol ratio was arrived 2 in formula 3 or so, it causes alcohol largely excessive, leads to that alcohol loss is higher in process of production and production control difficulty is larger.Resin simultaneously Last acid value 30-36 causes the relatively low of the degree of cross linking in powder, and paper-tear picture is relatively difficult in practical transfer process.CN10448265B A kind of low-temperature setting thermal transfer polyester resin for powder coating is disclosed, which adopts to realize low-temperature setting by improving Viscosity is reduced with butyl ethyl propylene glycol, while low-temperature setting is largely realized by the way of curing accelerator.Actual feedback Final template coating levelling is poor and weather resistance is relatively low, is unable to satisfy " GB/T 5237.4-2008 Alminum Project type The 4th part of material: dust profile " in requirement.It is poly- that CN102977346B discloses a kind of TGIC solidification weather-resistance powder coatings use Ester resin, however the acid value of final polyester resin, in 32-36, the relatively low degree of cross linking for making final coating of acid value is relatively low, unfavorable In thermal transfer.While the M-phthalic acid of its resin accounts for the content of resin 11% or so, weather resistance is relatively low, is unable to satisfy Requirement in " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: dust profile ".CN1023304790A is disclosed A kind of outdoor aluminum profile heat transfer printing powder coating polyester resin is pointed out in the patent to use a large amount of second in formula in description Base butyl propylene glycol, while newest standards " GB/T 5237.4-2008 aluminium is equally also unable to satisfy without M-phthalic acid in formula The 4th part of alloy architectural shape: dust profile " requirement.CN107778466A discloses a kind of HAA solidification thermal transfer powder Coating polyester resin is equally unable to satisfy " GB/T there is a large amount of ethylene glycol and diethylene glycol in the polyester resin The 4th part of 5237.4-2008 aluminum alloy building section: dust profile " in requirement about polyester resin, while being formulated middle-end The presence of hydroxy silicon oil can pollute reaction kettle, so that a possibility that product of production line switches is 0, therefore in actual production can not Using.
Summary of the invention
To solve the above problems, it is an object of the invention to provide a kind of hydroxyalkyl amides to solidify thermal transfer powdery paints end carboxylic Base saturated polyester resin and its synthetic method, the polyester resin have suitable glass transition temperature and color, resin component Meet the requirement in " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: dust profile " about polyester resin.Preparation At powder coating solidification after coating there is levelling and mechanical performance performance is good, weather resistance meets " GB/T 5237.4- The 4th part of 2008 aluminum alloy building section: dust profile " II grade standard, thermally transferred pattern it is clear and without offset printing, be applicable in In thermal transfer art of powder coatings.
The present invention provides a kind of hydroxyalkyl amide solidification thermal transfer powdery paints carboxyl end group saturated polyester resin, main It is formed by the raw material melt polycondensation of following weight percent: polyalcohol: 30-45%wt;Aromatic polycarboxylic acid 43-55%wt;Branching agent: 0.01-3%wt;Acidolysis agent: 8-18%wt;Esterification catalyst 0.03-0.15%wt;Antioxidant 0.01-2%wt.
The polyalcohol uses neopentyl glycol (NPG).More preferably using the neopentyl glycol of hydrogenation method production.
The branching agent is mixed using one of trimethylolpropane (TMP) and trimethylolethane (TME) or two kinds It closes.
The aromatic polycarboxylic acid is using the mixed of one of phthalic acid (PTA) and M-phthalic acid (IPA) or both Close object.
The antioxidant is using phosphite ester (three [2.4- di-tert-butyl-phenyl] phosphite esters, antioxidant 626) and is obstructed The side of phenolic antioxidant (four [β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol esters, antioxidant 1010) compounding Formula, the gross mass based on resin, usage amount are 0.01-2%wt.
The catalyst is tin catalyst, preferably Dibutyltin oxide, tributyltin oxide, dihydroxy butyl chlorination Tin, stannous oxalate, one of Mono-n-butyltin or several, the gross mass based on resin, usage amount are 0.03- 0.15%wt 。
The acidolysis agent is using M-phthalic acid (IPA), adipic acid (ADA), Isosorbide-5-Nitrae cyclohexane cyclohexanedimethanodibasic (CHDA) and rich horse The mixing of one or more of sour (FCC)
Its synthetic method are as follows: by the neopentyl glycol (NPG) of formula ratio, trimethyl propane (TMP), trimethylolethane (TME), throw Enter heating and melting in reaction kettle, then puts into aromatic acid and suitable catalyst in reaction kettle simultaneously, in nitrogen atmosphere slowly Be warming up to 235-255 DEG C and maintain, after system clarification after sample detection acid value (AV) reach 5-15 (unit mgKOH/g resin, under Secondary acidolysis agent IPA, ADA, CHDA and FCC etc. are added when together) and maintains to carry out acidolysis sealing end at 235-250 DEG C of temperature.To poly- The acid value of ester is cooled to 230-240 DEG C and vacuum polycondensation for a period of time when reaching 50-65, so that the acid value of polyester maintains 37- 55 or so and hydroxyl value less than 6.With being cooled to 180-230 DEG C of throwing antioxidant later and maintain blowing after 5-30min.
Mass fraction of the M-phthalic acid of carboxyl end group saturated polyester resin in polyester resin is greater than 15%
The number average molecular weight of carboxyl end group saturated polyester resin is in 2500-5000 g/mol, glass transition temperature (Tg) >=58 DEG C, 60 DEG C of more preferred Tg >.
The acid value of carboxyl end group saturated polyester resin is in 37-55 range and hydroxyl value < 6%, more preferably hydroxyl value≤4, in this way The polyester resin meets the feature of carboxyl end group.
Carboxyl end group saturated polyester resin and curing agent, pigment, filler, levelling agent and degasser etc., which can be prepared into, to be suitable for The powdery paints of thermal transfer.It the use of with the preparation step of powdery paints of the present invention is by qualified carboxyl end group saturated polyester tree Rouge is mixed respectively at curing agent, pigments and fillers and other auxiliary agents according to suitable ratio, melting extrusion, cooling is broken, being sieved is made Powdery paints.Pigments and fillers include titanium dioxide, barium sulfate, calcium carbonate etc., other auxiliary agents include levelling agent and degasser etc..
Carboxyl end group saturated polyester tree resin component satisfaction " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: Dust profile " in requirement about polyester resin.Coating after its powder coating solidification being prepared into has levelling and machinery Performance performance is good, weather resistance meets in " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: dust profile " II grade standard, thermally transferred pattern are clear and without offset printing, are suitable for outdoor thermal transfer art of powder coatings.
Hydroxyl value, the resin former material of acid value and < 6mgKOH/g of the carboxyl end group saturated polyester tree resin with 37-55mgKOH/g Not hydrogeneous polyalcohol, glass transition temperature >=63 DEG C, number-average molecular weight are in 2500-5000 or so in material.What it was prepared into With levelling and mechanical performance performance, good, weather resistance meets " GB/T 5237.4-2008 to coating after powder coating solidification The 4th part of aluminum alloy building section: dust profile " II grade standard, thermally transferred pattern it is clear and without offset printing, be suitable for heat Transfer art of powder coatings.
The synthetic method of carboxyl end group saturated polyester tree resin be specially according to formula by polyalcohol, aromatic polycarboxylic acid and branching Agent is placed in reaction kettle, and esterification catalyst is added and carries out esterifying polycondensation reaction at 180-255 DEG C;Acidolysis agent is added and carries out polycondensation And sealing end;230-240 DEG C and vacuum polycondensation are cooled to specified acid value;It is cooled to 180-230 DEG C of throwing antioxidant and maintains 5- Blowing after 30min.
Beneficial effects of the present invention: there is suitable glass transition temperature, storage stability and synthetic technology of resins letter The advantages such as list and resin are at low cost, resin component satisfaction " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: are dusted Profile " in requirement about polyester resin for powder coating, with HAA be used in conjunction made of coating after powder coating solidification have Levelling and mechanical performance performance is good, weather resistance satisfaction " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: is dusted Profile " II grade standard, thermally transferred pattern it is clear and without offset printing, be suitable for thermal transfer art of powder coatings.
Specific embodiment
In order to deepen the understanding of the present invention, the present invention will be described in further detail with reference to the examples below, the embodiment For explaining only the invention, it is not intended to limit the scope of the present invention..
A part of specific embodiment is set forth below, and the present invention will be described, in table 1 A ~ D be the embodiment of the present invention and Performance of its corresponding polyester resin.
Preparation method: in 5 liters of glass reaction kettles, the polyalcohol and branching agent heat temperature raising of proportional quantity listed by table 1 is added Fusing, then sequentially adds corresponding aromatic dibasic acid and catalyst, and logical nitrogen slowly heats up, and system is since 185 ~ 194 DEG C Esterification occurs and is discharged, is then gradually heated to 240 DEG C, coreaction about 3-5h to system is clarified, and system acid value reaches 10- 15mgKOH/g resin;Acidolysis agent is added and maintains 1-3h, so that the acid value of system reaches 50-65 mgKOH/g resin;In 230- Vacuum (- 0.1MPa) polycondensation 0.5-3h makes the acid value of system reach 37-55mgKOH/g resin at 240 DEG C;Then it is cooled to 180 DEG C investment 10g antioxidant 626 and 10g antioxidant 1010 to get arrive saturated polyester resin of the present invention.
1. carboxyl end group saturated polyester resin component of table and performance
The performance of the saturated polyester resin synthesized with the present embodiment can be embodied the performance of manufactured powdery paints.It incite somebody to action this Embodiment synthesis saturated polyester resin A ~ D respectively at T105, levelling agent, titanium dioxide, barium sulfate, styrax and 701B etc. according to Ratio in table 2 mixes after weighing up, and powdery paints is made after melting extrusion, tabletting, broken and sieving respectively with screw extruder. Then by powder paint on the metal plate after surface granosealing, the test body after 180 DEG C/15min solidification The various performances of system, the performance test results are shown in Table 2.Transfer scheme is the hot pressing 400s at 170 DEG C of hot plate, then tears paper Open observation transferring effect.
The composition and coating transfer performance of 2. powdery paints of table
Remarks: xenon lamp test method is shown in " the 4th part of GB/T 5237.4-2008 aluminum alloy building section: dust profile "
By saturated polyester resin A ~ D of the present embodiment synthesis respectively at T105, levelling agent, titanium dioxide, barium sulfate, delustering agent, peace Breath perfume and 701B etc. mix after weighing up according to the ratio in table 2, melt extrusion, tabletting, broken and mistake respectively with screw extruder Powdery paints is made after sieve.Then by powder paint on the metal plate after surface granosealing, through 180 DEG C/ The various performances of test system, the performance test results are shown in Table 2 after 15min solidifies.By table 2 it is known that figure layer levelling and machine Tool performance is excellent, and thermally transferred pattern is clearly without offset printing, xenon lamp 1000h light-protection rate > 90%.
The present invention can be described with others without prejudice to the concrete form of spirit or essential characteristics of the invention.The present invention The embodiment above can only all be considered the description to invention rather than limit, it is full to be such as not limited to carboxyl end group of the present invention With the one-step method preparation method of polyester resin.Using one-step method preparation method, i.e., by polyalcohol, aromatic polycarboxylic acid, aliphatic polyol The mode that acid, branching agent, acidolysis agent and esterification catalyst carry out esterification condensation reaction after mixing is prepared into saturated resin, It is available carboxyl end group saturated polyester resin of the present invention.Therefore all substantial technologicals according to the present invention are to the above reality Any trickle amendment, the equivalent variations modification that example is done are applied, is belonged in the range of technical solution of the present invention.

Claims (10)

1. a kind of hydroxyalkyl amide solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, it is characterised in that: by following The raw material melt polycondensation of weight percent forms: polyalcohol: 30-45%wt;Aromatic polycarboxylic acid 43-55%wt;Branching agent: 0.01- 3%wt;Acidolysis agent: 8-18%wt;Esterification catalyst 0.03-0.15%wt;Antioxidant 0.01-2%wt.
2. a kind of hydroxyalkyl amide as described in claim 1 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, It is characterized by: the polyalcohol uses neopentyl glycol, the neopentyl glycol is produced using hydrogenation method.
3. a kind of hydroxyalkyl amide as described in claim 1 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, It is characterized by: the branching agent is using one of trimethylolpropane and trimethylolethane or two kinds of mixing.
4. a kind of hydroxyalkyl amide as described in claim 1 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, It is characterized by: the aromatic polycarboxylic acid is using one of phthalic acid and M-phthalic acid or both mixing.
5. a kind of hydroxyalkyl amide as described in claim 1 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, It is characterized by: the antioxidant using phosphite ester and Hinered phenols antioxidant compounding by the way of, the gross mass based on resin, Its usage amount is 0.01-2%wt.
6. a kind of hydroxyalkyl amide as described in claim 1 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, It is characterized by: the esterification catalyst is tin catalyst, it is by Dibutyltin oxide, tributyltin oxide, dihydroxy fourth Base stannic chloride, stannous oxalate, one of Mono-n-butyltin or several compositions, the gross mass based on resin, usage amount It is 0.03-0.15%wt.
7. a kind of hydroxyalkyl amide as described in claim 1 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, It is characterized by: the acidolysis agent using one of M-phthalic acid, adipic acid, Isosorbide-5-Nitrae cyclohexane cyclohexanedimethanodibasic and fumaric acid or The a variety of mixing of person.
8. a kind of hydroxyalkyl amide as claimed in claim 4 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin, It is characterized by: mass fraction of the M-phthalic acid in polyester resin is greater than 15%.
9. a kind of hydroxyalkyl amide according to claims 1-8 solidifies thermal transfer powdery paints with carboxyl end group saturated polyester tree Rouge, it is characterised in that: the molecular weight of the polyester resin is in 2500-5000 g/mol, glass transition temperature >=58 DEG C, acid Value is in 37-55mgKOH/g range of resin and hydroxyl value < 6%.
10. a kind of hydroxyalkyl amide as claimed in claim 9 solidifies thermal transfer powdery paints carboxyl end group saturated polyester resin Synthetic method, it is characterised in that: the synthetic method are as follows: by the neopentyl glycol of formula ratio, trimethyl propane, trihydroxy methyl second Heating and melting in alkane, investment reaction kettle, then puts into aromatic acid and suitable catalyst in reaction kettle, simultaneously in nitrogen atmosphere It is to slowly warm up to 235-255 DEG C and maintains, be added two when sample detection acid value reaches 5-15mgKOH/g resin after system clarification Secondary acidolysis agent IPA, ADA, CHDA and FCC simultaneously maintains to carry out acidolysis sealing end at 235-250 DEG C of temperature;Acid value to polyester reaches 230-240 DEG C and vacuum polycondensation are cooled to when 50-65mgKOH/g resin, so that the acid value of polyester maintains 37-55mgKOH/g Resin and hydroxyl value is less than 6;With being cooled to 180-230 DEG C of throwing antioxidant later and maintain blowing after 5-30min.
CN201811458610.0A 2018-11-30 2018-11-30 A kind of hydroxyalkyl amide solidification thermal transfer powdery paints carboxyl end group saturated polyester resin and its synthetic method Pending CN109762145A (en)

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CN110305569A (en) * 2019-07-17 2019-10-08 浙江光华科技股份有限公司 A kind of polyester resin and preparation method thereof based on phenylsuccinic acid acid anhydride
CN110511365A (en) * 2019-08-15 2019-11-29 安徽神剑新材料股份有限公司 A kind of engineering machinery polyester resin
CN112048236A (en) * 2020-09-09 2020-12-08 黄山佳杰新材料科技有限公司 Extinction type thermal transfer powder coating and preparation method and application thereof
CN116804081A (en) * 2023-08-01 2023-09-26 安徽永昌新材料有限公司 Silicon-based curing type polyester resin, preparation method and application thereof
CN118064038A (en) * 2024-03-25 2024-05-24 四川睿智新材料科技有限公司 Hydroxyalkyl amide curing thermal transfer powder coating and preparation method and application thereof
CN118064038B (en) * 2024-03-25 2024-11-15 四川睿智新材料科技有限公司 Hydroxyalkyl amide curing thermal transfer powder coating and preparation method and application thereof

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Application publication date: 20190517