CN108503814A - A kind of epoxidized polyester resins and the preparation method and application thereof - Google Patents
A kind of epoxidized polyester resins and the preparation method and application thereof Download PDFInfo
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- CN108503814A CN108503814A CN201810379814.9A CN201810379814A CN108503814A CN 108503814 A CN108503814 A CN 108503814A CN 201810379814 A CN201810379814 A CN 201810379814A CN 108503814 A CN108503814 A CN 108503814A
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- Prior art keywords
- polyester resins
- epoxidized polyester
- epoxidized
- acid value
- raw material
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Classifications
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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
- C08G63/91—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
-
- 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
-
- 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
Abstract
The invention belongs to powder coating technology fields, and in particular to a kind of epoxidized polyester resins, and preparation method is further disclosed, and it is used to prepare the purposes of powdery paints.Epoxidized polyester resins of the present invention, with diethyl terephthalate, glutamic acid, dimercaptosuccinic acid, 12 hydroxy stearic acids, 1 diphenylphosphino ethane of dihydroxy, 2, 5 dimethyl 2, 5 hexylene glycols, neopentyl glycol, the material copolymerizations such as resorcinolformaldehyde resin are formed, the acid value of finally obtained polyester resin is less than 2mgKOH/g, epoxide equivalent is 800 900g/mol, 85 105 DEG C of softening point, it can be cured with commercially available high acid value carboxyl polyester (48 52mgKOH/g of acid value) instead of 12 epoxy resin of E, film fully achieves the requirement of powdery paints, powder coating, which is made, has preferable stability and water boiling resistance performance.
Description
Technical field
The invention belongs to powder coating technology fields, and in particular to a kind of epoxidized polyester resins, and it is further disclosed
Preparation method, and it is used to prepare the purposes of powdery paints.
Background technology
Powdery paints is a kind of 100% solid powder without organic solvent, it is different from oil paint and water paint,
Not using solvent or water as decentralized medium when application, but using air as decentralized medium, it is uniformly coated on workpiece surface, is passed through
A kind of new type environment friendly coating of one layer of film with specific use is formed after heating.Powdery paints has VOC free, environmental protection, section
Can, the advantages that construction efficiency height and application range is wide, and the advantages that, environmental protection economic with it, remarkable efficient and performance, just gradually replace
For organic solvent type coatings, become the important development direction in coating industry, is always maintained at faster growth rate.Polyesters
Powdery paints more with its excellent durability, dicoration and processing forming the features such as, be widely used in field of coating.
Traditional powdery paints polyester mostly be carboxyl polyester resin either hydroxy polyester resin, but the system polyester without
Method realizes that the self-curing of polyester system, institute's corresponding curing agent of addition in need realize solidification.By taking indoor powdery paints as an example,
It is often used E-12 epoxy resin and carries out collocation use with carboxyl polyester resin.But in above-mentioned traditional powder coating systems, due to
E-12 epoxy resin needs in the synthesis process using epoxychloropropane and sodium hydroxide to be raw material so that in E-12 epoxy resin
Containing a certain amount of sodium chloride and sodium hydroxide, the water boiling resistance performance of this powder coating all to finally preparing has certain unfavorable
It influences；Meanwhile the presence of chlorion also has metal base certain corrosiveness；Furthermore E-12 epoxy resin itself at
This is also relatively high.These all influence and limit the performance and stability of powdery paints to a certain extent.
Invention content
For this purpose, technical problem to be solved by the present invention lies in a kind of epoxidized polyester resins are provided, and further disclose
Preparation method；
Second technical problem that the present invention solves is to provide a kind of epoxidized polyester resins and is used to prepare powdery paints
Purposes.
In order to solve the above technical problems, a kind of epoxidized polyester resins of the present invention, with the epoxidized polyester tree
The total amount meter of fat, includes the raw material components of following molar percentage：
Preferably, the epoxidized polyester resins, in terms of the total amount of the epoxidized polyester resins, including following mole
The raw material components of percentage：
The epoxidized polyester resins further include esterification catalyst, and the mole dosage of the esterification catalyst accounts for described
The 0.05-0.25mol% of raw material components integral molar quantity.
The esterification catalyst includes di-t-butyl stannous chloride.
The epoxidized polyester resins further include antioxidant, and the mole dosage of the antioxidant accounts for the raw material components
The 0.1-0.3mol% of integral molar quantity.
The antioxidant includes antioxidant 300, i.e. 4,4'- thiobis (6- tertiary butyls metacresol).
The invention also discloses a kind of methods preparing the epoxidized polyester resins, include the following steps：
(1) a selected amount of diethyl terephthalate, dimercaptosuccinic acid and 12- hydroxy stearic acids are mixed, and controls temperature
Degree carries out heating melting less than 130 DEG C；
(2) a selected amount of dihydroxy -1- diphenylphosphino ethanes, 2,5- dimethyl -2,5- are added into above-mentioned mixed material
Hexylene glycol and neopentyl glycol, and a selected amount of catalyst is added, it is gradually warming up to 180 DEG C under nitrogen protection, and be added
A selected amount of glutamic acid mixing is then to slowly warm up to steam without apparent distillate, and the acid value of reactant is less than 25mgKOH/g
Until；
(3) a selected amount of antioxidant is added, and keeps the vacuum degree 2-4h of 40-60mmHg, to facilitate the shape of polyester resin
At stopping reaction when acid value is reduced to 12mgKOH/g or less；
(4) material is cooled to 140-150 DEG C, and a selected amount of resorcinolformaldehyde resin is added, kept the temperature
1-3h is reacted, stops reaction when the acid value of reactant is less than 2mgKOH/g, and high temperature discharging while hot through cooling, is crushed, makes
Grain to get.
In the step (2), the reaction temperature is no more than 235 DEG C.
The invention also discloses the purposes that the epoxidized polyester resins are used to prepare powdery paints.
The powdery paints is 60：40 type polyester powder coatings.
Epoxidized polyester resins of the present invention, with diethyl terephthalate, glutamic acid, dimercaptosuccinic acid, 12- hydroxyls
Base stearic acid, dihydroxy -1- diphenylphosphino ethanes, 2,5- dimethyl -2,5-HD, neopentyl glycol, resorcinol 2-glycidyl
The material copolymerizations such as ether are formed, and the acid value of finally obtained polyester resin is less than 2mgKOH/g, epoxide equivalent 800-900g/mol,
85-105 DEG C of softening point can replace E-12 epoxy resin to be carried out with commercially available high acid value carboxyl polyester (acid value 48-52mgKOH/g)
Solidification, film fully achieve the requirement of powdery paints, and powder coating, which is made, has preferable stability and water boiling resistance performance.
Epoxidized polyester resins of the present invention do not use epoxychloropropane and alkali in preparation process so that production eventually
Almost without the residual of any chloride, coating performance and metal base to powdery paints will not all have an impact product, and effectively drop
The low cost of powdery paints.
Specific implementation mode
Embodiment 1
Epoxidized polyester resins described in the present embodiment in terms of the total amount of the epoxidized polyester resins, including rub as follows
The raw material components of your percentage：
The preparation method of epoxidized polyester resins described in the present embodiment, includes the following steps：
(1) a selected amount of diethyl terephthalate, dimercaptosuccinic acid and 12- hydroxy stearic acids are added in mixer,
And it controls temperature and carries out heating melting less than 130 DEG C；
(2) a selected amount of dihydroxy -1- diphenylphosphino ethanes, 2,5- dimethyl -2,5- are added into above-mentioned mixed material
Hexylene glycol and neopentyl glycol, and a selected amount of catalyst is added, it is gradually warming up to 180 DEG C under nitrogen protection, and be added
A selected amount of glutamic acid mixing is then to slowly warm up to steam without apparent distillate, and the acid value of reactant is less than 25mgKOH/g
Until；And the reaction temperature for controlling whole process is no more than 235 DEG C；
(3) a selected amount of antioxidant 300 is added, and keeps the vacuum degree 2-4h of 40-60mmHg, to facilitate polyester resin
It is formed, stops reaction when acid value is reduced to 12mgKOH/g or less；
(4) material is cooled to 140-150 DEG C, and a selected amount of resorcinolformaldehyde resin is added, kept the temperature
1-3h is reacted, stops reaction when the acid value of reactant is less than 2mgKOH/g, and high temperature discharging while hot through cooling, is crushed, makes
Grain to get.
After testing, acid value 0.7mgKOH/g, the epoxide equivalent 829g/mol of epoxidized polyester resins obtained by the present embodiment,
98 DEG C of softening point.
Embodiment 2
Epoxidized polyester resins described in the present embodiment in terms of the total amount of the epoxidized polyester resins, including rub as follows
The raw material components of your percentage：
The preparation method is the same as that of Example 1 for epoxidized polyester resins described in the present embodiment.
After testing, acid value 0.9mgKOH/g, the epoxide equivalent 842g/mol of epoxidized polyester resins obtained by the present embodiment,
101 DEG C of softening point.
Embodiment 3
Epoxidized polyester resins described in the present embodiment in terms of the total amount of the epoxidized polyester resins, including rub as follows
The raw material components of your percentage：
The preparation method is the same as that of Example 1 for epoxidized polyester resins described in the present embodiment.
After testing, acid value 0.5mgKOH/g, the epoxide equivalent 870g/mol of epoxidized polyester resins obtained by the present embodiment,
98 DEG C of softening point.
Embodiment 4
Epoxidized polyester resins described in the present embodiment in terms of the total amount of the epoxidized polyester resins, including rub as follows
The raw material components of your percentage：
The preparation method is the same as that of Example 1 for epoxidized polyester resins described in the present embodiment.
After testing, acid value 0.8mgKOH/g, the epoxide equivalent 810g/mol of epoxidized polyester resins obtained by the present embodiment,
95 DEG C of softening point.
Embodiment 5
Epoxidized polyester resins described in the present embodiment in terms of the total amount of the epoxidized polyester resins, including rub as follows
The raw material components of your percentage：
The preparation method is the same as that of Example 1 for epoxidized polyester resins described in the present embodiment.
After testing, acid value 1.5mgKOH/g, the epoxide equivalent 892g/mol of epoxidized polyester resins obtained by the present embodiment,
89 DEG C of softening point.
Embodiment 6
Epoxidized polyester resins described in the present embodiment in terms of the total amount of the epoxidized polyester resins, including rub as follows
The raw material components of your percentage：
The preparation method is the same as that of Example 1 for epoxidized polyester resins described in the present embodiment.
After testing, acid value 1.2mgKOH/g, the epoxide equivalent 884g/mol of epoxidized polyester resins obtained by the present embodiment,
86 DEG C of softening point.
Comparative example 1
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing to benzene two
Formic acid diethylester.
After testing, the acid value 0.9mgKOH/g of gained epoxidized polyester resins, epoxide equivalent 819g/mol, softening point 75
℃。
Comparative example 2
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing glutamic acid.
After testing, the acid value 1.1mgKOH/g of gained epoxidized polyester resins, epoxide equivalent 836g/mol, softening point 79
℃。
Comparative example 3
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing sulfydryl fourth
Diacid.
After testing, the acid value 0.8mgKOH/g of gained epoxidized polyester resins, epoxide equivalent 830g/mol, softening point
106℃。
Comparative example 4
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing 12- hydroxyls
Stearic acid.
After testing, the acid value 0.9mgKOH/g of gained epoxidized polyester resins, epoxide equivalent 839g/mol, softening point
113℃。
Comparative example 5
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing dihydroxy-
1- diphenylphosphino ethanes.
After testing, the acid value 0.7mgKOH/g of gained epoxidized polyester resins, epoxide equivalent 833g/mol, softening point 90
℃。
Comparative example 6
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing 2,5- bis-
Methyl -2,5-HD.
After testing, the acid value 15mgKOH/g of gained epoxidized polyester resins, epoxide equivalent 846g/mol, softening point 120
℃。
Comparative example 7
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing new penta 2
Alcohol.
After testing, the acid value 0.7mgKOH/g of gained epoxidized polyester resins, epoxide equivalent 834g/mol, softening point 88
℃。
Comparative example 8
Polyester resin described in this comparative example to prepare raw material same as Example 1, differ only in without containing isophthalic two
Phenol diglycidyl ether.
After testing, the acid value 10mgKOH/g of gained epoxidized polyester resins, epoxide equivalent are more than 10000g/mol, softening
109 DEG C of point.
Experimental example
Polyester resin made from 1-6 of the embodiment of the present invention and comparative example 1-8 is taken respectively, and progress is grouped as according to following group
60：It is prepared by 40 type polyester powder coatings：
And (acid value is less than 1mgKOH/g, epoxide equivalent 846g/ with conventional use of E-12 epoxy resin in the prior art
Mol, 94 DEG C of softening point) replace epoxidized polyester resins of the present invention as a comparison case 9.
According to 60：Each material mixing with double screw extruder extrusion, tabletting, is crushed, so by 40 polyester powder coating formulas
Sheet stock is pulverized and sieved afterwards, powdery paints is made.Gained powdery paints is sprayed on the Ma Kou after surface treated using electrostatic gun
On iron-based material, cure to get paint coatings through 180 DEG C/15min.
Coating Indexs measure foundation is GB/T 21776-2008《The examination criteria guide of powdery paints and its coating》, and
The every detection data of record is in the following table 1.
1 performance powder coating detection data of table
Epoxidized polyester resins of the present invention are can be seen that from upper table data, it can be with current 60：40 type carboxyl polyesters
Resin is cured, and for being used in indoor powdery paints, has preferable comprehensive performance.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. a kind of epoxidized polyester resins, which is characterized in that in terms of the total amount of the epoxidized polyester resins, prepare raw material packet
Include the raw material components of following molar percentage：
2. epoxidized polyester resins according to claim 1, which is characterized in that with the total amount of the epoxidized polyester resins
Meter, includes the raw material components of following molar percentage：
3. epoxidized polyester resins according to claim 1 or 2, which is characterized in that further include esterification catalyst, the ester
The mole dosage for changing catalyst accounts for the 0.05-0.25mol% of the raw material components integral molar quantity.
4. epoxidized polyester resins according to claim 3, which is characterized in that the esterification catalyst includes di-t-butyl
Stannous chloride.
5. according to claim 1-4 any one of them epoxidized polyester resins, which is characterized in that further include antioxidant, it is described
The mole dosage of antioxidant accounts for the 0.1-0.3mol% of the raw material components integral molar quantity.
6. epoxidized polyester resins according to claim 5, which is characterized in that the antioxidant includes antioxidant 300.
7. a kind of method preparing claim 1-6 any one of them epoxidized polyester resins, which is characterized in that including as follows
Step：
(1) a selected amount of diethyl terephthalate, dimercaptosuccinic acid and 12- hydroxy stearic acids are mixed, and it is low to control temperature
Heating melting is carried out in 130 DEG C；
(2) be added into above-mentioned mixed material a selected amount of dihydroxy -1- diphenylphosphino ethanes, 2,5- dimethyl -2,5- oneself two
Alcohol and neopentyl glycol, and a selected amount of catalyst is added, it is gradually warming up to 180 DEG C under nitrogen protection, and be added selected
The glutamic acid mixing of amount is then to slowly warm up to steam without apparent distillate, and the acid value of reactant is less than 25mgKOH/g
Only；
(3) a selected amount of antioxidant is added, and the vacuum degree 2-4h of 40-60mmHg is kept to be waited for facilitate the formation of polyester resin
Acid value stops reaction when being reduced to 12mgKOH/g or less；
(4) material is cooled to 140-150 DEG C, and a selected amount of resorcinolformaldehyde resin is added, carry out insulation reaction
1-3h stops reaction, and high temperature discharging while hot when the acid value of reactant is less than 2mgKOH/g, through cooling, broken, granulation, i.e.,
.
8. the method according to claim 8 for preparing the epoxidized polyester resins, which is characterized in that the step (2)
In, the reaction temperature is no more than 235 DEG C.
9. claim 1-6 any one of them epoxidized polyester resins are used to prepare the purposes of powdery paints.
10. purposes according to claim 9, which is characterized in that the powdery paints is 60：40 type polyester powder coatings.
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| CN201810379814.9A CN108503814B (en) | 2018-04-25 | 2018-04-25 | Epoxidized polyester resin and preparation method and application thereof |
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| CN201810379814.9A CN108503814B (en) | 2018-04-25 | 2018-04-25 | Epoxidized polyester resin and preparation method and application thereof |
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| CN109762539A (en) * | 2019-02-15 | 2019-05-17 | 北京启顺京腾科技有限责任公司 | A kind of New drilling fluid oil lubricant and its synthetic method |
| CN115612380A (en) * | 2022-10-26 | 2023-01-17 | 安徽永利新材料科技有限公司 | Indoor mixed powder coating polyester resin and preparation method thereof |
| CN115895438A (en) * | 2022-12-27 | 2023-04-04 | 捷科冉(厦门)新材料有限公司 | Transparent organic silicon coating for polycarbonate surface and preparation method thereof |
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| CN115895438B (en) * | 2022-12-27 | 2024-02-13 | 捷科冉(厦门)新材料有限公司 | Transparent organic silicon coating for polycarbonate surface and preparation method thereof |
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