CN106366233B - A kind of hydrophobic antifouling function solid propenoic acid matting resin - Google Patents
A kind of hydrophobic antifouling function solid propenoic acid matting resin Download PDFInfo
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- CN106366233B CN106366233B CN201610716143.1A CN201610716143A CN106366233B CN 106366233 B CN106366233 B CN 106366233B CN 201610716143 A CN201610716143 A CN 201610716143A CN 106366233 B CN106366233 B CN 106366233B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
- C09D5/033—Powdery paints characterised by the additives
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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
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1687—Use of special additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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Abstract
The present invention provides a kind of hydrophobic antifouling function solid propenoic acid matting resin, component includes other vinyl monomers of the fluoroacrylate monomer, 17-25wt% of 5-10wt% vinyl monomer and 78-65wt% containing glycidyl solid ring oxygroup acrylic type matting resin modified through free-radical polymerized synthesis.The solid ring oxygroup acrylic type matting resin of modification provided by the invention is used in outdoor powdery paints, and acquired film is not only able to satisfy requirement of the people to low smooth appearance, and the smooth degree of film and hydrophobic antifouling performance be improved significantly.
Description
Technical field
The present invention relates to powder paint compositions delustering agent technical fields, and in particular to a kind of modification is suitable for powder
The epoxy group acrylic type matting resin of last coating composition.
Background technique
The dulling and curing agent that epoxy group acrylic type solid propenoic acid resin can be used as saturated carboxyl polyester uses, and is production
One of the main material of outdoor extinction powder coating.This kind of powdery paints be generally used for automobile, household electrical appliances, outdoor building building materials,
On the objects such as ship, outdoor sports utensil, the film of formation can meet the weather resistance and comfortable of outdoor application simultaneously
Matt appearance.It is well known that invasion of the coating of outdoor application vulnerable to rainwater and pollutants in air, cause
Coating need to be cleaned often, be repeatedly subjected to wear, so as to shorten service life.
Summary of the invention
In order to solve the above technical problems, the present invention provides a kind of hydrophobic antifouling function solid propenoic acid matting resin,
It is formed including following parts by weight:
The fluoroacrylate monomer of 5-10wt%,
Vinyl monomer of the 17-25wt% containing glycidyl,
Other vinyl monomers of 78-65wt% epoxy group acrylic type matting resin modified through free-radical polymerized synthesis.
Preferably, the fluoroacrylate monomer is acrylic acid trifluoro ethyl ester, trifluoroethyl methacrylate, third
Five fluorine propyl ester of olefin(e) acid, five fluorine propyl ester of methacrylic acid, methacrylic acid octafluoro pentyl ester, 17 fluorine nonyl ester of methacrylic acid, methyl
One of 17 fluorine last of the ten Heavenly stems ester of acrylic acid a variety of is used in mixed way.
Preferably, the fluoroacrylate monomer is five fluorine propyl ester of acrylic acid trifluoro ethyl ester and/or acrylic acid.
Preferably, wherein the epoxy group acrylic type matting resin number-average molecular weight of the modification is 7000-25000, glass
Glass temperature is 30 DEG C -100 DEG C, and epoxide equivalent is 500-900 grams/equivalent.
Preferably, the epoxy group acrylic type matting resin number-average molecular weight of the modification is 8000-15000, vitrifying
Temperature is 40 DEG C -80 DEG C, and epoxide equivalent is 550-850 grams/equivalent.
Preferably, wherein the epoxy group acrylic type matting resin of the modification is copolymerized using free radical solution polymerization method
Synthesis, using one or both of toluene, dimethylbenzene, ethyl acetate, butyl cellosolve, cyclohexanone mixture；Select azo
One of bis-isobutyronitrile, cumyl peroxide, peroxidating phenyl-diformyl, two t-amyl peroxy compounds are a variety of as freely
Base initiator.
Preferably, wherein the usage amount of radical initiator is 0.5-5%.
Preferably, wherein the epoxy group acrylic type matting resin makes as saturated carboxyl polyester dulling and curing agent
With.
The invention has the following advantages:
The present invention passes through the modification to epoxy group acrylic type matting resin, acquired new epoxy group acrylic type delustring
Resin is in powdery paints, film to be not only able to satisfy requirement of the people to low gloss appearance after solidification, but also film is smooth
Degree and hydrophobic antifouling performance are improved, and can often be cleaned to avoid coating, cleaning abrasion are reduced, to extend service life.
The epoxy group acrylic type matting resin of this modification is in automobile, household electrical appliances, outdoor building building materials, ship, outdoor sports utensil etc.
Industry field is with a wide range of applications.The modified matting resin of the present invention can be used as saturated carboxyl polyester dulling and curing agent
It uses.The epoxy group acrylic type matting resin of modification provided by the invention is used in saturated polyester, is re-dubbed powdery paints, Gu
The coating formed after change, not only keeps good extinction effect, but also the hydrophobic stain resistant performance of obtained film and smooth
Degree is significantly improved.The product of this modification compensates for the demand in market, there is the very big market space and implementary value.
Certainly, it implements any of the products of the present invention and does not necessarily require achieving all the advantages described above at the same time.
Specific embodiment
The technical solution in the present invention is clearly and completely described below in conjunction with the embodiment of the present invention, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
All other embodiment obtained by those of ordinary skill in the art without making creative efforts, belongs to this hair
The range of bright protection.
Embodiment 1
By the glycidyl methacrylate of 40g, the methyl methacrylate of 100g, 50g ethyl methacrylate,
The styrene of 10g, the peroxidating phenyl-diformyl of 3.5g are made into dropwise addition mixed solution.200g dimethylbenzene is added three mouthfuls of 1000ml
In flask and the stirring that heats up after solvent refluxing starts that mixed solution is added dropwise, and about 2.5-3h is dripped, and continues back flow reaction 2h,
0.5g peroxidating phenyl-diformyl is added, back flow reaction 3h is further continued for.Neat solvent is steamed at reduced pressure conditions, temperature is no more than 180 DEG C,
201g epoxy group acrylic matting resin 1 is made in blowing, cooling, coarse crushing while hot, and measuring its glass transition temperature is 78.5 DEG C,
Number-average molecular weight is about 9055, and epoxide equivalent is 709 grams/equivalent.
Embodiment 2
By the acrylic acid trifluoro ethyl ester of 6g, the glycidyl methacrylate of 44g, 100g methyl methacrylate,
The ethyl methacrylate of 40g, the styrene of 10g, 3.5g peroxidating phenyl-diformyl be made into dropwise addition mixed solution.By 200g ring
Hexanone is added in the three-necked flask of 1000ml and the stirring that heats up, and after solvent refluxing, starts that mixed solution, about 2.5-3h drop is added dropwise
It adds, continues back flow reaction 2h, add 0.5g peroxidating phenyl-diformyl, be further continued for back flow reaction 3h.It steams at reduced pressure conditions net
Solvent, temperature are no more than 180 DEG C, and 199g epoxy group acrylic matting resin 2, measurement is made in blowing, cooling, coarse crushing while hot
Its glass transition temperature is 74 DEG C, and number-average molecular weight is about 9550, and epoxide equivalent is 640 grams/equivalent.
Embodiment 3
By the acrylic acid trifluoro ethyl ester of 10g, the glycidyl methacrylate of 40g, 100g methyl methacrylate,
The ethyl methacrylate of 40g, the styrene of 10g, 3.5g peroxidating phenyl-diformyl be made into dropwise addition mixed solution.By 200g ring
Hexanone is added in the three-necked flask of 1000ml and the stirring that heats up, and after solvent refluxing, starts that mixed solution, about 2.5-3h drop is added dropwise
It adds, continues back flow reaction 2h, add 0.5g peroxidating phenyl-diformyl, be further continued for back flow reaction 3h.It steams at reduced pressure conditions net
Solvent, temperature are no more than 180 DEG C, and 199g epoxy group acrylic matting resin 3, measurement is made in blowing, cooling, coarse crushing while hot
Its glass transition temperature is 35 DEG C, and number-average molecular weight is about 7500, and epoxide equivalent is 550 grams/equivalent.
Embodiment 4
By the acrylic acid trifluoro ethyl ester of 20g, the glycidyl methacrylate of 50g, 100g isobutyl
Ester, the ethyl acrylate of 15g, the styrene of 15g, 3.5g peroxidating phenyl-diformyl be made into dropwise addition mixed solution.By 200g ring
Hexanone is added in the three-necked flask of 1000ml and the stirring that heats up, and after solvent refluxing, starts that mixed solution, about 2.5-3h drop is added dropwise
It adds, continues back flow reaction 2h, add 0.5g peroxidating phenyl-diformyl, be further continued for back flow reaction 3h.It steams at reduced pressure conditions net
Solvent, temperature are no more than 180 DEG C, and 202g epoxy group acrylic matting resin 4, measurement is made in blowing, cooling, coarse crushing while hot
Its glass transition temperature is 73.5 DEG C, and number-average molecular weight is about 10000, and epoxide equivalent is 706 grams/equivalent.
Embodiment 5
By the acrylic acid trifluoro ethyl ester of 10g, the trifluoroethyl methacrylate of 10g, 50g methyl propenoic acid glycidyl
Ester, the Isobutyl methacrylate of 100g, the styrene of 30g, 3.5g azodiisobutyronitrile be made into dropwise addition mixed solution.It will
200g ethyl acetate is added in the three-necked flask of 1000ml and the stirring that heats up, and after solvent refluxing, starts that mixed solution is added dropwise, about
2.5-3h is dripped, and is continued back flow reaction 2h, is added 0.5g azodiisobutyronitrile, be further continued for back flow reaction 3h.In reduced pressure
Lower steaming neat solvent, temperature are no more than 180 DEG C, and 197.8g epoxy group acrylic matting tree is made in blowing, cooling, coarse crushing while hot
Rouge 5, measuring its glass transition temperature is 53 DEG C, and number-average molecular weight is about 12000, and epoxide equivalent is 570 grams/equivalent.
Embodiment 6
By the five fluorine propyl ester of acrylic acid of 10g, the glycidyl methacrylate of 34g, 100g isobutyl
Ester, 26g isopropyl methacrylate, the styrene of 30g, 8.5g peroxidating phenyl-diformyl be made into dropwise addition mixed solution.It will
200g ethyl acetate is added in the three-necked flask of 1000ml and the stirring that heats up, and after solvent refluxing, starts that mixed solution is added dropwise, about
2.5-3h is dripped, and is continued back flow reaction 2h, is added 1.5g peroxidating phenyl-diformyl, be further continued for back flow reaction 3h.In decompression item
Neat solvent is steamed under part, temperature is no more than 180 DEG C, and 202.8g epoxy group acrylic matting is made in blowing, cooling, coarse crushing while hot
Resin 6, measuring its glass transition temperature is 50 DEG C, and number-average molecular weight is about 14500, and epoxide equivalent is 826 grams/equivalent.
Table 1 is that (isocyanuric acid three contracts epoxy group acrylic matting resin of the present invention in saturated carboxyl polyester powdery paints
Water glyceride (TGIC) be co-curing agent) application performance formula, table 2 be epoxy group acrylic type matting resin of the present invention satisfying
With the application performance formula of (hydroxyalkyl amide is as co-curing agent) in carboxyl polyester powdery paints, by table 1 formula 1-6 and
Formula 7-12 in table 2 carries out ingredient, then mixes the mixture prepared by high-speed mixer, mixed material
Tabletting is squeezed out by double screw extruder, extruder extrusion temperature is set as 100 DEG C, after tabletting material is by pulverizer crushing, then
After the sieving of 180 mesh screens, powder coating formulation 1-12 is made respectively, is specifically shown in Tables 1 and 2.Formulation for coating material 1-12 is used
The method of electrostatic spraying sprays on stainless steel respectively, toasts 10 minutes at 200 DEG C, and finally obtaining dried film thickness is 90um, point
The other performance test that film is carried out to each formula, is specifically shown in Table 3.
The performance test methods and evaluation criterion of film are as follows:
The smooth degree of film indicates that pencil hardness test method is referring to GB/T6739-2006 using pencil hardness.
The glossiness of film is tested and evaluation is referring to GB/T 9754-2007.
The contact angle test and evaluation method of film: taking the test board prepared, measures film using contact angle instrument
With the contact angle of water.Contact angle is greater than 90 °, illustrates the hydrophobic ability for having certain, contact angle is bigger, and film coated surface can be lower, says
The hydrophobicity of bright film is better.
The resistance to soiling and evaluation method and evaluation criterion of coating are as follows:
Red permanent pen resistance to soiling: painting dye is carried out to film prepared above with red permanent pen, keeps 24
After hour, is gently wiped with the dipped cotton balls of methanol, then observe remaining spot.Evaluation criterion is as follows:
5: there is no spot 4: almost without spot 3: light soil 2: many spots 1: serious spot
Table 1
Remarks: 1.: polyester resin, Wuhu mind sword Chemical Manufacture.
2.: the polyacrylate levelling agent of Worlee company production.
3.: filler, the production of Guizhou Hua Jia company.4.: carbon black, Mitsubishi Corporation of Japan production.
Table 2
Remarks: 5.: prompt sensible Chemical Manufacture is pacified in hydroxy alkyl amide curing agents, Anhui six.
It can be seen from Table 3 that being free of bloom hydrophobic antifouling function provided by the invention in comparative formula 1 and comparative formula 7
Can solid propenoic acid matting resin, the smooth degree of film is poor after solidification, the contact angle of film and water is lower than 90 °, while film
Stain resistant is poor.It can from the test result of the formula of the epoxy group acrylic type matting resin containing modification of the invention
Out, the contact angle of the smooth degree of film and film and water is obviously improved, while the stain resistant of film is preferable.From 2 Hes of formula
The test result of formula 8 can be seen that when the dosage of fluorinated acrylic ester is lower, and the stain resistant of film is also by certain journey
The influence of degree.In addition, a certain amount of fluorinated acrylic ester is added from table 3 it is observed that the glossiness of cured coating film is lower
Class monomer to the gloss of film not
There is any influence.
Table 3
Present invention disclosed above preferred embodiment is only intended to help to illustrate the present invention.There is no detailed for preferred embodiment
All details are described, are not limited the invention to the specific embodiments described.Obviously, according to the content of this specification,
It can make many modifications and variations.These embodiments are chosen and specifically described to this specification, is in order to better explain the present invention
Principle and practical application, so that skilled artisan be enable to better understand and utilize the present invention.The present invention is only
It is limited by claims and its full scope and equivalent.
Claims (5)
1. a kind of hydrophobic antifouling function solid propenoic acid matting resin, which is characterized in that formed including following parts by weight:
The fluoroacrylate monomer of 5-10wt%,
Vinyl monomer of the 17-25wt% containing glycidyl,
Other vinyl monomers of 78-65wt% epoxy group acrylic type matting resin modified through free-radical polymerized synthesis；
The fluoroacrylate monomer is acrylic acid trifluoro ethyl ester, trifluoroethyl methacrylate, five fluorine third of acrylic acid
Ester, five fluorine propyl ester of methacrylic acid, methacrylic acid octafluoro pentyl ester, 17 fluorine nonyl ester of methacrylic acid, methacrylic acid 17
One of fluorine last of the ten Heavenly stems ester a variety of is used in mixed way；
The epoxy group acrylic type matting resin number-average molecular weight of the modification be 7000-25000, glass transition temperature be 30 DEG C-
100 DEG C, epoxide equivalent is 500-900 grams/equivalent；
The epoxy group acrylic type matting resin is used as saturated carboxyl polyester dulling and curing agent；
The fouling resistance rating of film is 5 after the hydrophobic antifouling function solid propenoic acid matting resin solidifies.
2. hydrophobic antifouling function solid propenoic acid matting resin according to claim 1, which is characterized in that the fluorination
Acrylic ester monomer is five fluorine propyl ester of acrylic acid trifluoro ethyl ester and/or acrylic acid.
3. hydrophobic antifouling function solid propenoic acid matting resin according to claim 1, which is characterized in that the modification
Epoxy group acrylic type matting resin number-average molecular weight is 8000-15000, and glass transition temperature is 40 DEG C-80 DEG C, epoxide equivalent
For 550-850 grams/equivalent.
4. hydrophobic antifouling function solid propenoic acid matting resin according to claim 1, which is characterized in that described in wherein
Modified epoxy group acrylic type matting resin use free radical solution polymerization method copolymerization, solvent using toluene, dimethylbenzene,
One or both of ethyl acetate, butyl cellosolve, cyclohexanone mixture；Select azodiisobutyronitrile, peroxidating diisopropyl
One of benzene, peroxidating phenyl-diformyl, two t-amyl peroxy compounds are a variety of as radical initiator.
5. hydrophobic antifouling function solid propenoic acid matting resin according to claim 4, which is characterized in that wherein free radical
The usage amount of initiator is 0.5-5%.
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| CN107629165B (en) * | 2017-10-16 | 2020-07-07 | 六安捷通达新材料有限公司 | Hydroxyl type solid acrylic extinction resin and preparation method thereof |
| CN109535902B (en) * | 2018-10-15 | 2021-01-15 | 西安理工大学 | Preparation method of super-amphiphobic coating for surface of wood-plastic composite material |
| CN115895416A (en) * | 2021-08-18 | 2023-04-04 | 贝内克-长顺汽车内饰材料（张家港）有限公司 | Coating composition for leather surface and corresponding leather |
| CN117070134B (en) * | 2023-10-07 | 2023-12-26 | 佛山市南海嘉多彩粉末涂料有限公司 | Corrosion-resistant outdoor extinction powder coating composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1865368A (en) * | 2006-04-27 | 2006-11-22 | 兰州理工大学 | GMA fluorocarbon acrylic acid powdery paints and its preparation method |
| CN101952379A (en) * | 2008-02-22 | 2011-01-19 | 巴斯夫欧洲公司 | Fluoro levelling agents |
| CN104927505A (en) * | 2015-06-18 | 2015-09-23 | 巨化集团技术中心 | Thermoset fluororesin powder coating preparation method |
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2016
- 2016-08-24 CN CN201610716143.1A patent/CN106366233B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1865368A (en) * | 2006-04-27 | 2006-11-22 | 兰州理工大学 | GMA fluorocarbon acrylic acid powdery paints and its preparation method |
| CN101952379A (en) * | 2008-02-22 | 2011-01-19 | 巴斯夫欧洲公司 | Fluoro levelling agents |
| CN104927505A (en) * | 2015-06-18 | 2015-09-23 | 巨化集团技术中心 | Thermoset fluororesin powder coating preparation method |
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