CN108794802A - The preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating - Google Patents
The preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating Download PDFInfo
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- CN108794802A CN108794802A CN201810740345.9A CN201810740345A CN108794802A CN 108794802 A CN108794802 A CN 108794802A CN 201810740345 A CN201810740345 A CN 201810740345A CN 108794802 A CN108794802 A CN 108794802A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/26—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing carboxylic acid groups, their anhydrides or esters
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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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating, ester exchange reaction and esterification are carried out using PEN waste materials and polyalcohol, polyacid, catalyst Mono-n-butyltin, stabilizer phosphite ester triphenylmethyl methacrylate, after ester exchange reaction and esterification, carry out depressurization condensation reaction, trimellitic anhydride, the progress degree of polymerization adjustment reaction of 18 tertiary amine of curing agent are added after depressurization condensation reaction, and impurity is removed by filtration after reaction and obtains polyester resin.The present invention realizes the recycling of waste and old PEN, reduces pollutions of the waste and old PEN to environment；Simultaneously compared with traditional handicraft compared with material cost reduces degree and reaches 30% or more, and polyester resin prepared by this method has higher glass transition temperature, while possessing preferable gloss, impact resistance and excellent levelling.
Description
Technical field
The present invention relates to polyester resin to prepare technical field, and in particular to a kind of high glass transition temperature hybrid thermosetting powder
The preparation method of last coating polyester resin.
Background technology
Currently, domestic thermosetting powder coating is mainly made of resin, curing agent, color stuffing, auxiliary agent etc., it is broadly divided into pure
Polyester powder coating and mixed powder coating are mainly used in the fields such as household metal furniture, electrical accessorie, hardware component.
Mixed powder coating is also known as epoxy-polyester type thermosetting powder coating, mostly by aromatic series hydroxy acid（Or acid anhydrides）It is passed through with polyalcohol
Thermosetting property saturated polyester resin is made in polycondensation reaction.It is polyester polyol, ethylene glycol, diethylene glycol (DEG) that polyalcohol, which mostly uses, or it is mixed
Object is closed, aromatic series hydroxy acid is mainly PTA（P-phthalic acid）, it is aided with trimellitic anhydride.Due to polyacid selection limitation,
It cannot meet polyester property requirement using single polyalcohol, generally require to carry out rational allocation use to a variety of alcohol, in the hope of making to gather
Ester performance reaches best.In general, to improve polyester property and stability, generally require to increase solid alcohol（Neopentyl glycol）'s
Content, and the price of solid alcohol is more expensive, also increases polyester cost.It is right especially in temperature higher season and region
Polyester resin glass transition temperature it is more demanding, still carried out in a manner of increasing solid alcohol content in production of polyester link at this stage
Adjustment, effect can not meet application demand while increasing cost.
Invention content
The present invention provides a kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating,
To solve, production cost of the existing technology is higher and the undesirable technical problem of glass transition temperature.
The technical solution adopted by the present invention to solve the technical problems is：
A kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating, using the poly- naphthalene two of recycling
Formic acid second diester PEN waste materials, PEN waste materials crush after with polyalcohol, polyacid, catalyst Mono-n-butyltin, stabilizer phosphorous
Acid esters triphenylmethyl methacrylate carries out ester exchange reaction and esterification, and after ester exchange reaction and esterification, it is anti-to carry out decompression polycondensation
It answers, trimellitic anhydride, the progress degree of polymerization adjustment reaction of 18 tertiary amine of curing agent is added after depressurization condensation reaction, instead
Impurity is removed by filtration after answering and obtains polyester resin.
Above-mentioned PEN waste materials melting temperature is 170~235 DEG C, need to be ground into the particle of 5 mm~10mm grain sizes.
Above-mentioned polyalcohol is ethylene glycol, diethylene glycol (DEG), triethylene glycol, neopentyl glycol, 2- methyl-1s, 3- propylene glycol, 1,3-
Propylene glycol, propylene glycol, butanediol, special pentanediol and trimethylolpropane it is one or more.
Above-mentioned polyacid be M-phthalic acid, p-phthalic acid, stearic acid, adipic acid, maleic acid, trimellitic anhydride and
Phthalic anhydride it is one or more.
Above-mentioned polyalcohol addition accounts for the 100%~300% of PEN mass；Mono-n-butyltin account for PEN mass 0.25%~
0.6%；Polyacid accounts for the 300%~650% of PEN mass；Phosphite ester triphenylmethyl methacrylate accounts for the 0.3%~0.8% of PEN mass；Trimellitic acid
Acid anhydride accounts for the 15%~28% of PEN mass；18 tertiary amines account for the 2.5%~5% of PEN mass.
Above-mentioned transesterification and esterification reaction temperature are 190 DEG C~250 DEG C；Transesterification and esterification termination condition are：It takes
It is 30 ± 5mgKOH/g that sample, which analyzes acid value, and viscosity is 30 ± 10cSt, and viscosimeter test temperature is 150 ± 5 DEG C.
Above-mentioned depressurization condensation reaction condition is：Reacting kettle inner pressure≤0.095Mpa, 230~250 DEG C of temperature；Described subtracts
Pressure polycondensation reaction termination condition be：Sampling analysis viscosity reaches 15 ± 10cSt, and viscosimeter temperature is 200 ± 5 DEG C, and acid value reaches
To 15 ± 10mgKOH/g, hydroxyl value reaches < 5mgKOH/g.
Reacting kettle inner pressure control is in 0.09 Mpa~0.095Mpa in above-mentioned depressurization condensation reaction.
The above-mentioned degree of polymerization adjusts reaction condition：200 ± 5 DEG C of reaction temperature；Termination condition is reacted in degree of polymerization adjustment：
Sampling analysis acid value is 50~55mgKOH/g, and viscosity is 25 cSt~35cSt, and viscosimeter temperature is 200 ± 5 DEG C, hydroxyl value <
5mgKOH/g。
The method of the present invention is produced using PEN material class waste materials, is realized the recycling of waste and old PEN, is reduced waste and old
Pollutions of the PEN to environment has significant environmental benefit；Simultaneously compared with traditional handicraft compared with material cost reduces degree and reaches 30%
More than, while polyester resin prepared by this method has higher glass transition temperature, while possessing preferable gloss, shock resistance
Property, excellent levelling, meet the requirement to polyester fiberglass in powdery paints production process.
Specific implementation mode
Example 1
A kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating, using the poly- naphthalene two of recycling
Formic acid second diester PEN waste materials, PEN waste material melting temperatures are 170~235 DEG C, after need to being ground into the particle of 5 mm~10mm grain sizes
Ester exchange reaction is carried out with polyalcohol, polyacid, catalyst Mono-n-butyltin, stabilizer phosphite ester triphenylmethyl methacrylate and esterification is anti-
It answers, polyalcohol is ethylene glycol, diethylene glycol (DEG), triethylene glycol, neopentyl glycol, 2- methyl-1s, 3- propylene glycol, 1,3- propylene glycol, third
Glycol, butanediol, special pentanediol and trimethylolpropane it is one or more, polyacid is M-phthalic acid, smart terephthaldehyde
Acid, stearic acid, adipic acid, maleic acid, trimellitic anhydride and phthalic anhydride it is one or more, polyalcohol addition accounts for
The 200% of PEN mass；Mono-n-butyltin accounts for the 0.45% of PEN mass；Polyacid accounts for the 420% of PEN mass；Phosphite ester triphen
Ester accounts for the 0.5% of PEN mass, and transesterification and esterification reaction temperature are 190 DEG C~250 DEG C；Transesterification and esterification termination condition
For：Sampling analysis acid value is 30 ± 5mgKOH/g, and viscosity is 30 ± 10cSt, and viscosimeter test temperature is 150 ± 5 DEG C, and ester is handed over
After changing reaction and esterification, depressurization condensation reaction is carried out, depressurization condensation reaction condition is：Reacting kettle inner pressure control exists
0.09 Mpa~0.095Mpa, 230~250 DEG C of temperature；The depressurization condensation reaction termination condition is：Sampling analysis viscosity
Reaching 15 ± 10cSt, viscosimeter temperature is 200 ± 5 DEG C, and acid value reaches 15 ± 10mgKOH/g, and hydroxyl value reaches < 5mgKOH/g,
Trimellitic anhydride is added after depressurization condensation reaction, 18 tertiary amine of curing agent carries out degree of polymerization adjustment reaction, inclined benzene
Three acid anhydrides account for the 30% of PEN mass；18 tertiary amines account for the 3% of PEN mass, and degree of polymerization adjustment reaction condition is：Reaction temperature
200±5℃；Termination condition is reacted in degree of polymerization adjustment：Sampling analysis acid value be 50~55mgKOH/g, viscosity be 25 cSt~
35cSt, viscosimeter temperature are 200 ± 5 DEG C, and hydroxyl value < 5mgKOH/g are removed by filtration impurity and obtain polyester after reaction
Resin.
Example 2
A kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating, using the poly- naphthalene two of recycling
Formic acid second diester PEN waste materials, PEN waste material melting temperatures are 170~235 DEG C, after need to being ground into the particle of 5 mm~10mm grain sizes
Ester exchange reaction is carried out with polyalcohol, polyacid, catalyst Mono-n-butyltin, stabilizer phosphite ester triphenylmethyl methacrylate and esterification is anti-
It answers, polyalcohol is ethylene glycol, diethylene glycol (DEG), triethylene glycol, neopentyl glycol, 2- methyl-1s, 3- propylene glycol, 1,3- propylene glycol, third
Glycol, butanediol, special pentanediol and trimethylolpropane it is one or more, polyacid is M-phthalic acid, smart terephthaldehyde
Acid, stearic acid, adipic acid, maleic acid, trimellitic anhydride and phthalic anhydride it is one or more, polyalcohol addition accounts for
The 100% of PEN mass；Mono-n-butyltin accounts for the 0.25% of PEN mass；Polyacid accounts for the 230% of PEN mass；Phosphite ester triphen
Ester accounts for the 0.3% of PEN mass, and transesterification and esterification reaction temperature are 190 DEG C~250 DEG C；Transesterification and esterification termination condition
For：Sampling analysis acid value is 30 ± 5mgKOH/g, and viscosity is 30 ± 10cSt, and viscosimeter test temperature is 150 ± 5 DEG C, and ester is handed over
After changing reaction and esterification, depressurization condensation reaction is carried out, depressurization condensation reaction condition is：Reacting kettle inner pressure control exists
0.09 Mpa~0.095Mpa, 230~250 DEG C of temperature；The depressurization condensation reaction termination condition is：Sampling analysis viscosity
Reaching 15 ± 10cSt, viscosimeter temperature is 200 ± 5 DEG C, and acid value reaches 15 ± 10mgKOH/g, and hydroxyl value reaches < 5mgKOH/g,
Trimellitic anhydride is added after depressurization condensation reaction, 18 tertiary amine of curing agent carries out degree of polymerization adjustment reaction, inclined benzene
Three acid anhydrides account for the 20% of PEN mass；18 tertiary amines account for the 2.1% of PEN mass, and degree of polymerization adjustment reaction condition is：Reaction temperature
200 ± 5 DEG C of degree；Termination condition is reacted in degree of polymerization adjustment：Sampling analysis acid value is 50~55mgKOH/g, and viscosity is 25 cSt
~35cSt, viscosimeter temperature are 200 ± 5 DEG C, and hydroxyl value < 5mgKOH/g are removed by filtration impurity and are gathered after reaction
Ester resin.
Example 3
A kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating, using the poly- naphthalene two of recycling
Formic acid second diester PEN waste materials, PEN waste material melting temperatures are 170~235 DEG C, after need to being ground into the particle of 5 mm~10mm grain sizes
Ester exchange reaction is carried out with polyalcohol, polyacid, catalyst Mono-n-butyltin, stabilizer phosphite ester triphenylmethyl methacrylate and esterification is anti-
It answers, polyalcohol is ethylene glycol, diethylene glycol (DEG), triethylene glycol, neopentyl glycol, 2- methyl-1s, 3- propylene glycol, 1,3- propylene glycol, third
Glycol, butanediol, special pentanediol and trimethylolpropane it is one or more, polyacid is M-phthalic acid, smart terephthaldehyde
Acid, stearic acid, adipic acid, maleic acid, trimellitic anhydride and phthalic anhydride it is one or more, polyalcohol addition accounts for
The 300% of PEN mass；Mono-n-butyltin accounts for the 0.6% of PEN mass；Polyacid accounts for the 650% of PEN mass；Phosphite ester triphen
Ester accounts for the 0.8% of PEN mass, and transesterification and esterification reaction temperature are 190 DEG C~250 DEG C；Transesterification and esterification termination condition
For：Sampling analysis acid value is 30 ± 5mgKOH/g, and viscosity is 30 ± 10cSt, and viscosimeter test temperature is 150 ± 5 DEG C, and ester is handed over
After changing reaction and esterification, depressurization condensation reaction is carried out, depressurization condensation reaction condition is：Reacting kettle inner pressure control exists
0.09 Mpa~0.095Mpa, 230~250 DEG C of temperature；The depressurization condensation reaction termination condition is：Sampling analysis viscosity
Reaching 15 ± 10cSt, viscosimeter temperature is 200 ± 5 DEG C, and acid value reaches 15 ± 10mgKOH/g, and hydroxyl value reaches < 5mgKOH/g,
Trimellitic anhydride is added after depressurization condensation reaction, 18 tertiary amine of curing agent carries out degree of polymerization adjustment reaction, inclined benzene
Three acid anhydrides account for the 28% of PEN mass；18 tertiary amines account for the 5% of PEN mass, and degree of polymerization adjustment reaction condition is：Reaction temperature
200±5℃；Termination condition is reacted in degree of polymerization adjustment：Sampling analysis acid value be 50~55mgKOH/g, viscosity be 25 cSt~
35cSt, viscosimeter temperature are 200 ± 5 DEG C, and hydroxyl value < 5mgKOH/g are removed by filtration impurity and obtain polyester after reaction
Resin.
Claims (9)
1. a kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating, it is characterized in that using back
The polyethylene naphthalate PEN waste materials of receipts, PEN waste materials crush after with polyalcohol, polyacid, catalyst Mono-n-butyltin,
Stabilizer phosphite ester triphenylmethyl methacrylate carries out ester exchange reaction and esterification, after ester exchange reaction and esterification, carries out
Depressurization condensation reaction adds trimellitic anhydride after depressurization condensation reaction, 18 tertiary amine of curing agent carries out the degree of polymerization
Adjustment reaction, is removed by filtration impurity and obtains polyester resin after reaction.
2. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 1
Method, it is characterized in that PEN is the recycling PEN waste materials of variously-shaped various performances, melting temperature is 170~235 DEG C.
3. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 1
Method, it is characterized in that polyalcohol is ethylene glycol, diethylene glycol (DEG), triethylene glycol, neopentyl glycol, 2- methyl-1s, 3- propylene glycol, 1,3-
Propylene glycol, propylene glycol, butanediol, special pentanediol and trimethylolpropane it is one or more.
4. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 1
Method, it is characterized in that polyacid be M-phthalic acid, p-phthalic acid, stearic acid, adipic acid, maleic acid, trimellitic anhydride and
Phthalic anhydride it is one or more.
5. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 1
Method, it is characterized in that polyalcohol addition accounts for the 100%~300% of PEN mass；Mono-n-butyltin account for PEN mass 0.25%~
0.6%；Polyacid accounts for the 300%~650% of PEN mass；Phosphite ester triphenylmethyl methacrylate accounts for the 0.3%~0.8% of PEN mass；Trimellitic acid
Acid anhydride accounts for the 15%~28% of PEN mass；18 tertiary amines account for the 2.5%~5% of PEN mass.
6. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 1
Method, it is characterized in that transesterification and esterification reaction temperature are 190 DEG C~250 DEG C；Transesterification and esterification termination condition are：Sampling
Analysis acid value is 30 ± 5mgKOH/g, and viscosity is 30 ± 10cSt, and viscosimeter test temperature is 150 ± 5 DEG C.
7. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 1
Method, it is characterized in that depressurization condensation reaction condition is：Reacting kettle inner pressure≤0.095Mpa, 230~250 DEG C of temperature；Described subtracts
Pressure polycondensation reaction termination condition be：Sampling analysis viscosity reaches 15 ± 10cSt, and viscosimeter temperature is 200 ± 5 DEG C, and acid value reaches
To 15 ± 10mgKOH/g, hydroxyl value reaches < 5mgKOH/g.
8. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 7
Method, it is characterized in that reacting kettle inner pressure control is in 0.09 Mpa~0.095Mpa in depressurization condensation reaction.
9. the preparation side of high glass transition temperature hybrid thermosetting polyester resin for powder coating according to claim 1
Method, it is characterized in that degree of polymerization adjustment reaction condition is：200 ± 5 DEG C of reaction temperature；Termination condition is reacted in degree of polymerization adjustment：It takes
It is 50~55mgKOH/g that sample, which analyzes acid value, and viscosity is 25 cSt~35cSt, and viscosimeter temperature is 200 ± 5 DEG C, hydroxyl value <
5mgKOH/g。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110467873A (en) * | 2019-08-20 | 2019-11-19 | 德州名将工贸有限公司 | A kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating |
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2018
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| CN110467873A (en) * | 2019-08-20 | 2019-11-19 | 德州名将工贸有限公司 | A kind of preparation method of high glass transition temperature hybrid thermosetting polyester resin for powder coating |
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Application publication date: 20181113 |
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