CN105801820A - Method for preparing saturated polyester resin - Google Patents
Method for preparing saturated polyester resin Download PDFInfo
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- CN105801820A CN105801820A CN201610231588.0A CN201610231588A CN105801820A CN 105801820 A CN105801820 A CN 105801820A CN 201610231588 A CN201610231588 A CN 201610231588A CN 105801820 A CN105801820 A CN 105801820A
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- polyester resin
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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
-
- 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
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl 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
- 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
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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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- 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 method for preparing saturated polyester resin.Dimethyl terephthalate, neopentyl glycol, ethanediol and zinc acetate are added to a reaction still, the temperature is slowly raised during stirring, meanwhile, nitrogen is introduced for protection, and after the temperature is raised to 150 DEG C, the temperature is kept constant; a transesterification reaction is carried out for 3-5 hours, then trimellitic anhydride, terephthalic acid and phthalic anhydride are added, nitrogen continues to be introduced for protection, the temperature is raised to 170 DEG C to 240 DEG C under the action of zinc acetate, and an esterification reaction is carried out for 3-5 hours till a solution in the reaction still is clear and free of bubbles; triphenyl phosphate is added and stirred for 3-4 minutes, then vacuumizing is carried out, a polycondensation reaction is carried out for 1-1.5 hours, the reaction temperature is kept at 240 DEG C to 250 DEG C, and the vacuum degree ranges from 0.08 MPa to 0.095 MPa; nitrogen is used for vacuum elimination after the reaction is finished, and the temperature is reduced to 165 DEG C to 175 DEG C; after sebacic acid and adipic acid are added, the temperature is raised to 180 DEG C to 200 DEG C, an acetifying reaction is carried out, and the reaction is finished after sealing is carried out for 1.5 hours.The obtained polyester resin has good storage stability and the characteristic of the high acid value.
Description
Present patent application is the divisional application of invention and created name " high acid value saturated polyester resin of a kind of stable storing and preparation method thereof ", and the applying date of original application is on March 18th, 2015, and application number is 2015101182641.
Technical field
The invention belongs to outdoor powder coating technical field, relate to the high acid value saturated polyester resin of a kind of stable storing, the preparation method further relating to the high acid value saturated polyester resin of this kind of stable storing.
Background technology
Thermosetting polyester epoxy powder coating is with polyester resin for main film forming substance, adds the components such as epoxy resin, levelling agent, auxiliary agent, pigment, filler.The working procedure processing such as blended, melted makes powdery paints, on electrostatic spraying product after phosphatization, in certain temperature, in the time, is solidified into film that is smooth, hard and that have flexibility after resin melting, crosslinking.Film after solidification will not soften again because of the rising two of temperature.This coating is solvent-free, pollution-free, 100% film forming, both resource-saving, economizes again the energy.The characteristics such as coating has glossiness height, good leveling property, and paint film is plentiful, of light color, resistance to yellowing i.e. good ultraviolet resistance.It is widely used in the external coatings such as electric refrigerator, washing machine, vacuum cleaner and various meter case, bicycle, barred window fence, furniture, compared with acrylic acid powder coatings, there is better adhesive force, mechanical strength and application, workability.
Thermosetting polyester epoxy powder coating polyester resin divides saturated and unsaturated two big classes, ideal with saturation type polyester resin, has good weatherability and gloss retention.Saturation type polyester resin has oh type and carboxyl type two kinds, and oh type is generally firming agent with isocyanate etc., and carboxyl type is generally firming agent with the resin containing epoxide group.
Summary of the invention
The preparation method that it is an object of the invention to provide the high acid value saturated polyester resin of a kind of stable storing, makes the polyester resin of preparation have good shelf-stability, and vitrification point is high, and chemical-resistance is good, and flow leveling is excellent, has the characteristic of high acid value.
For solving technical problem, the present invention adopts the following technical scheme that
A kind of saturated polyester resin preparation method, saturated polyester resin raw material includes following components, and each component is respectively as follows: according to weight portion
nullIts preparation process includes: add dimethyl terephthalate (DMT) in a kettle.、Neopentyl glycol、Ethylene glycol and zinc acetate，Slowly heat up while stirring，Pass into nitrogen protection simultaneously，Constant temperature is kept after being warming up to 150 DEG C，Carry out ester exchange reaction 3～5 hours，It is subsequently adding trimellitic anhydride、P-phthalic acid and phthalic anhydride，Continue to pass into nitrogen protection，170～240 DEG C it are warming up under the effect of zinc acetate，Carry out esterification 3～5 hours，Until in reactor when solution clarification and bubble-free，Add triphenyl，Stir 3～4 minutes，Then evacuation，Carry out polycondensation reaction 1～1.5 hour，Reaction temperature is maintained at 240～250 DEG C，Vacuum is 0.08～0.095MPa，Reaction disappears vacuum with nitrogen after terminating，It is cooled to 165～175 DEG C，After adding decanedioic acid and adipic acid，It is warming up to 180～200 DEG C，Carry out acetifying reaction，Close 1.5 as a child reactions to terminate，Obtain the high acid value saturated polyester resin product of stable storing.
The curing accelerator of quaternary ammonium salt has been made into modified tertiary amines curing accelerator by the present invention, more stable in stable storing performance.Relative molecular mass size and the distribution thereof of resin are relevant with the amount of substance of alkyd when synthesis technique, vitrification point is main and the compliance of macromolecular chain, relative molecular weight and distribution, crystallization etc. are relevant, affect the bin stability of powdery paints, general vitrification point is more high, and the bin stability of powder is more good.The vitrification point of mixed polyester resin generally requires more than 50 DEG C, the heat resistance of softening point major decision resin and easy cooling, the melting viscosity of resin is main relevant with intermolecular amount of force and acid number, affect the levelability of powder coating, general resin melting viscosity is more little, and coating leveling is more good.
Compared with prior art, the method have the advantages that
Present invention employs vacuum polycondensation depolymerization, by polyhydric alcohol, polyacid monomer and esterification catalyst carry out ester exchange reaction, esterification is carried out again with anhydride, it is subsequently adding triphenyl and carries out vacuum polycondensation, add antacid and auxiliary agent carries out acetifying reaction, finally give the polyester resin with specific acid number of light yellow clear, the polyester resin obtained has good shelf-stability, vitrification point is up to 57～63 DEG C, chemical-resistance is good, viscosity is low to moderate 2500～3500mPa s, flow leveling is excellent, acid number is up to 57～63mgKOH/g, it is particularly well-suited to outdoor powdery paints.
Below in conjunction with detailed description of the invention, the invention will be further described:
Detailed description of the invention
The high acid value saturated polyester resin embodiment 1 of a kind of stable storing of the present invention, including following components, each component is respectively as follows: according to weight portion
nullThe preparation method of the high acid value saturated polyester resin of this kind of stable storing is as follows: add dimethyl terephthalate (DMT) in a kettle.、Neopentyl glycol、Ethylene glycol and zinc acetate，Slowly heat up while stirring，Pass into nitrogen protection simultaneously，Constant temperature is kept after being warming up to 150 DEG C，Carry out ester exchange reaction 3～5 hours，It is subsequently adding trimellitic anhydride、P-phthalic acid and phthalic anhydride，Continue to pass into nitrogen protection，170～240 DEG C it are warming up under the effect of zinc acetate，Carry out esterification 3～5 hours，Until in reactor when solution clarification and bubble-free，Add triphenyl，Stir 3～4 minutes，Then evacuation，Carry out polycondensation reaction 1～1.5 hour，Reaction temperature is maintained at 240～250 DEG C，Vacuum is 0.08～0.095Mpa，Reaction disappears vacuum with nitrogen after terminating，It is cooled to 165～175 DEG C，After adding decanedioic acid and adipic acid，It is warming up to 180～200 DEG C，Carry out acetifying reaction，Close 1.5 as a child reactions to terminate，Obtain the high acid value saturated polyester resin product of stable storing.
The high acid value saturated polyester resin embodiment 2 of a kind of stable storing of the present invention, including following components, each component is respectively as follows: according to weight portion
The preparation method of the high acid value saturated polyester resin of this kind of stable storing is identical with embodiment 1.
The high acid value saturated polyester resin embodiment 3 of a kind of stable storing of the present invention, including following components, each component is respectively as follows: according to weight portion
The preparation method of the high acid value saturated polyester resin of this kind of stable storing is identical with embodiment 1.
The high acid value saturated polyester resin embodiment 4 of a kind of stable storing of the present invention, including following components, each component is respectively as follows: according to weight portion
The preparation method of the high acid value saturated polyester resin of this kind of stable storing is identical with embodiment 1.
Saturated polyester resin comparative example of the prior art, including following components, each component is respectively as follows: according to weight portion
The preparation method of this kind of saturated polyester resin is as follows: reactor is heated to 95～100 DEG C, add neopentyl glycol, M-phthalic acid and titanium dioxide, slowly heat up while stirring, pass into nitrogen protection simultaneously, constant temperature is kept after being warming up to 245 DEG C, react 12～15 hours, until reactant clarification and acid number are at 42～48mgKOH/g, then evacuation, vacuum is 0.06～0.08Mpa, until reactant viscosity is at 4500～5500mPa s, acid number is at 32～34mgKOH/g, stop evacuation, cool to 200～210 DEG C, add antioxidant, stir 0.5 hour, obtain saturated polyester resin product.
Hardening time etc. at the acid number of high acid value saturated polyester resin product of the stable storing that embodiment 1～4 obtains, viscosity, vitrification point, softening point and 180 DEG C being detected, is compared with the prior art example simultaneously and compares, testing result is as shown in table 1.
Table 1
Test result shows, the acid number of the high acid value saturated polyester resin product of the stable storing that the embodiment of the present invention 1～4 obtains is at 60 ± 3mgKOH/g, and viscosity is at 3000 ± 500mPa s, and vitrification point is at 60 ± 3 DEG C, softening point is at 115 ± 10 DEG C, and the hardening time at 180 DEG C is at 12 ± 2min.The vitrification point of embodiment 1～4 is suitable with comparative example, but softening point is significantly improved than comparative example, illustrate that heat resistance increases to some extent, ratio of viscosities comparative example is decreased obviously, illustrate that its flow leveling is more excellent than comparative example, acid number is significantly larger than comparative example, there is the characteristic of specific acid number, hardening time at 180 DEG C is greatly reduced than comparative example, prior art can be accomplished 20 ± 2min preferably, the present invention but can drop to 12 ± 2min, illustrate to solidify the required time shorter, it is substantially better than comparative example, the combination property of visible product is all significantly improved than prior art.
When content one timing of ethylene glycol, the viscosity of resin is on a declining curve along with the increase of neopentyl glycol content；When not neopentyl glycol containing, the viscosity of resin declines along with the increase of ethylene glycol content；Along with the increase of adipic acid content, the viscosity of resin, softening point and vitrification point also decline within the specific limits to some extent.Therefore, the ratio of viscosities embodiment 1 of embodiment 2 has further decline, and its flow leveling also improves relatively, although vitrification point, softening point also slightly decline, but it is few to decline.And the ratio of viscosities embodiment 3 of embodiment 4 also has further decline, vitrification point, softening point are also substantially suitable, but decline to some extent hardening time, it is seen then that embodiment 2 and embodiment 4 are comparatively ideal embodiment.
It addition, the evaluation of stable storing performance:
By standard, sample is carried out the evaluation of powder thermosetting bin stability, the high acid value saturated polyester resin product of the stable storing that Example 1～4 obtains and each 100g sample of comparative example, it is individually placed to bottom test tube, clog test tube to place 7 days under 40 DEG C of isoperibols, after the time, take out test tube cool down 2 hours, by sample on the clean surface, observe sample phenomenon and draw evaluation, comparative example powdery paints occurs that slight compacting phenomenon is assessed as 1 grade, embodiment 1～4 powdery paints is all unchanged, it is assessed as 0 grade, illustrate that the product of the embodiment of the present invention 1～4 is more stable than prior art comparative example in stable storing performance.
Chemical-resistance is evaluated:
With acetone and MEK, high acid value saturated polyester resin product and the comparative example of the stable storing that embodiment 1～4 obtains are carried out wipe test respectively, to the comparison carrying out gloss loss and pencil hardness before and after wiping, being dropped to about the 8% of embodiment 1～4 with the gloss loss of acetone wiping by the 15% of comparative example, pencil hardness is increased to the HB of embodiment 1～4 by the B of comparative example；Being dropped to about the 12% of embodiment 1～4 with the gloss loss of MEK wiping by the 20% of comparative example, pencil hardness is increased to the HB of embodiment 1～4 by the B of comparative example；Illustrate that embodiment 1～4 obtains than comparative example on chemical-resistance to be obviously improved.
The foregoing is only specific embodiments of the invention, but the technical characteristic of the present invention is not limited thereto, any those skilled in the art is in the field of the invention, and change or the modification made all are encompassed among the scope of the claims of the present invention.
Claims (1)
1. a saturated polyester resin preparation method, it is characterised in that: saturated polyester resin raw material includes following components, and each component is respectively as follows: according to weight portion
nullIts preparation process includes: add dimethyl terephthalate (DMT) in a kettle.、Neopentyl glycol、Ethylene glycol and zinc acetate，Slowly heat up while stirring，Pass into nitrogen protection simultaneously，Constant temperature is kept after being warming up to 150 DEG C，Carry out ester exchange reaction 3～5 hours，It is subsequently adding trimellitic anhydride、P-phthalic acid and phthalic anhydride，Continue to pass into nitrogen protection，170～240 DEG C it are warming up under the effect of zinc acetate，Carry out esterification 3～5 hours，Until in reactor when solution clarification and bubble-free，Add triphenyl，Stir 3～4 minutes，Then evacuation，Carry out polycondensation reaction 1～1.5 hour，Reaction temperature is maintained at 240～250 DEG C，Vacuum is 0.08～0.095MPa，Reaction disappears vacuum with nitrogen after terminating，It is cooled to 165～175 DEG C，After adding decanedioic acid and adipic acid，It is warming up to 180～200 DEG C，Carry out acetifying reaction，Close 1.5 as a child reactions to terminate，Obtain the high acid value saturated polyester resin product of stable storing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610231588.0A CN105801820A (en) | 2015-03-18 | 2015-03-18 | Method for preparing saturated polyester resin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610231588.0A CN105801820A (en) | 2015-03-18 | 2015-03-18 | Method for preparing saturated polyester resin |
| CN201510118264.1A CN104788653B (en) | 2015-03-18 | 2015-03-18 | A kind of high acid value saturated polyester resin of stable storing and preparation method thereof |
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| CN201510118264.1A Division CN104788653B (en) | 2015-03-18 | 2015-03-18 | A kind of high acid value saturated polyester resin of stable storing and preparation method thereof |
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| CN201610231663.3A Pending CN105837802A (en) | 2015-03-18 | 2015-03-18 | Preparation method of saturated polyester resin with high acid value and storage stability |
| CN201510118264.1A Active CN104788653B (en) | 2015-03-18 | 2015-03-18 | A kind of high acid value saturated polyester resin of stable storing and preparation method thereof |
| CN201610231588.0A Pending CN105801820A (en) | 2015-03-18 | 2015-03-18 | Method for preparing saturated polyester resin |
| CN201610230922.0A Pending CN105985513A (en) | 2015-03-18 | 2015-03-18 | High-storage-stability high-acid-value saturated polyester resin |
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| CN201610231663.3A Pending CN105837802A (en) | 2015-03-18 | 2015-03-18 | Preparation method of saturated polyester resin with high acid value and storage stability |
| CN201510118264.1A Active CN104788653B (en) | 2015-03-18 | 2015-03-18 | A kind of high acid value saturated polyester resin of stable storing and preparation method thereof |
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| CN111333827B (en) * | 2020-04-22 | 2022-06-10 | 黄山市源润新材料科技有限公司 | High-hardness and high-stability 60/40 mixed type polyester resin for powder and preparation method thereof |
Citations (4)
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|---|---|---|---|---|
| US4275189A (en) * | 1980-02-28 | 1981-06-23 | Cargill, Incorporated | Neopentyl glycol, terephthalate, dicarboxy acid, trimellitate thermosetting resin |
| CN101704939A (en) * | 2009-11-18 | 2010-05-12 | 黄山永佳三利科技有限公司 | Polyester resin used for powder coating and preparation method thereof |
| CN102295761A (en) * | 2011-07-11 | 2011-12-28 | 华润包装材料有限公司 | Method for preparing polyester for foaming |
| CN103304789A (en) * | 2013-06-06 | 2013-09-18 | 广东伊诗德新材料科技有限公司 | 6:4 type polyester resin with good water boiling resistance and preparation method thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101775124B (en) * | 2010-02-11 | 2012-07-25 | 东华大学 | Method for preparing abrasion-resistant scratch-resistant stable transparent polyester paint substrate |
| CN102433067A (en) * | 2011-08-29 | 2012-05-02 | 安徽省六安市立华电工有限公司 | Novel polyester enamelled wire paint and its preparation method |
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2015
- 2015-03-18 CN CN201610231663.3A patent/CN105837802A/en active Pending
- 2015-03-18 CN CN201510118264.1A patent/CN104788653B/en active Active
- 2015-03-18 CN CN201610231588.0A patent/CN105801820A/en active Pending
- 2015-03-18 CN CN201610230922.0A patent/CN105985513A/en active Pending
Patent Citations (4)
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|---|---|---|---|---|
| US4275189A (en) * | 1980-02-28 | 1981-06-23 | Cargill, Incorporated | Neopentyl glycol, terephthalate, dicarboxy acid, trimellitate thermosetting resin |
| CN101704939A (en) * | 2009-11-18 | 2010-05-12 | 黄山永佳三利科技有限公司 | Polyester resin used for powder coating and preparation method thereof |
| CN102295761A (en) * | 2011-07-11 | 2011-12-28 | 华润包装材料有限公司 | Method for preparing polyester for foaming |
| CN103304789A (en) * | 2013-06-06 | 2013-09-18 | 广东伊诗德新材料科技有限公司 | 6:4 type polyester resin with good water boiling resistance and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 《实用化学品配方手册》编委会: "《实用化学品配方手册》", 31 March 2009 * |
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| Publication number | Publication date |
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| CN105985513A (en) | 2016-10-05 |
| CN105837802A (en) | 2016-08-10 |
| CN104788653A (en) | 2015-07-22 |
| CN104788653B (en) | 2016-08-24 |
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