CN105949859B - A kind of powdery paints optical brightener and preparation method and application - Google Patents
A kind of powdery paints optical brightener and preparation method and application Download PDFInfo
- Publication number
- CN105949859B CN105949859B CN201610363870.4A CN201610363870A CN105949859B CN 105949859 B CN105949859 B CN 105949859B CN 201610363870 A CN201610363870 A CN 201610363870A CN 105949859 B CN105949859 B CN 105949859B
- Authority
- CN
- China
- Prior art keywords
- optical brightener
- powdery paints
- tert
- perfluorocyclohexyl
- butyl acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 53
- 239000003973 paint Substances 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title abstract description 4
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims abstract description 29
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000000843 powder Substances 0.000 claims abstract description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 9
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- -1 butenoic acid Ester Chemical class 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 6
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 23
- 239000011248 coating agent Substances 0.000 abstract description 21
- WIMBFQPYJQMSCP-UHFFFAOYSA-N (1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F WIMBFQPYJQMSCP-UHFFFAOYSA-N 0.000 abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 abstract description 6
- 238000009835 boiling Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 3
- 230000035939 shock Effects 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- JLQBGPTWZUVLHZ-UHFFFAOYSA-N 2-methyl-3-(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)prop-2-enoic acid Chemical compound OC(=O)C(C)=CC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F JLQBGPTWZUVLHZ-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 125000005459 perfluorocyclohexyl group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000010148 water-pollination Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/14—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Abstract
The invention belongs to powder coating technology fields, and in particular to a kind of powdery paints optical brightener and preparation method and application.The raw material composition of powdery paints optical brightener of the present invention includes：Dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylate, and end-capping reagent, initiator and organic solvent are added in, it is made through copolyreaction.The compatibility of powdery paints optical brightener and powdery paints of the present invention is more preferable, can preferably soak base material, improve adhesive force, is made that the shock resistance of coating is more excellent, and film-forming is excellent and the levelability of powdery paints is more preferable；Optical brightener of the present invention performance of adding lustre to is apparent, can prepare high glaze powdery paints and be used；And fluoro raw material improves the water resistance of optical brightener, boiling ability significantly improves.
Description
Technical field
The invention belongs to powder coating technology fields, and in particular to a kind of powdery paints optical brightener and preparation method thereof with
Using.
Background technology
The advantages that powdery paints is with its economic, environmental protection, remarkable efficient and performance, just gradually substitutes organic solvent type coatings,
As the important development direction in coating industry, faster growth rate is always maintained at.Especially polyesters powdery paints is more
The features such as with its excellent durability, dicoration and processing forming, it is widely used in field of coating.
Powdery paints be usually using resinous matter as film forming matter, add in curing agent, be aided with levelling agent, auxiliary agent, pigment,
The components such as filler, optical brightener are processed into powdery paints through the processes such as mixing, melting.The powdery paints through electrostatic spraying in
On treated product, in certain temperature, in the time, resin melting, crosslinking solidify afterwards are into smooth, hard and flexible
Film.Film after curing will not again soften due to the rise of temperature, and the coating is solvent-free, pollution-free, 100% film forming,
Not only resource is saved, but also saves the energy.And the coating that the powdery paints for being with the addition of optical brightener obtains after hardening have glossiness it is high,
Paint film is plentiful, color suitable for etc. characteristics.
Optical brightener, also known as brightener, are a kind of powder coating additives based on acrylate copolymer.Due to its point
Containing a certain number of polarity genes in son, therefore to the polarity additive (such as pigment, filler) in powdery paints and by painting base
Material (metals such as such as iron, aluminium) has good wetting action, so as in the manufacture and work progress of powdery paints, effectively rise
To shrinkage cavity, flake, pin hole is eliminated, coating gloss is improved, improves the levelling effect and flatness of powder coating, promotes to bottom village
Wettability and improve pigment dispersiveness.
But traditional powdery paints optical brightener is typically all using butyl acrylate homopolymerization or butyl acrylate and first
Base methyl acrylate copolymer is made, but the molecular structure of traditional optical brightener is relatively single, and causes and powdery paints body
The compatibility of system is poor, and since the hydrophily of general optical brightener is strong, and hydrophobic chain segment is then inadequate, holds in use
Easy coating of moving out, the water boiling resistance performance that can especially cause powdery paints are slightly worse, it would be highly desirable to improve.
The content of the invention
For this purpose, the technical problems to be solved by the invention are to provide a kind of preferable with the compatibility of powdery paints, add lustre to
Performance is apparent, and the preferable powdery paints optical brightener of water resistance.
In order to solve the above technical problems, powdery paints optical brightener of the present invention, mainly by acrylate and butylene
Acid esters is made of raw material through copolyreaction, and the raw material composition of the optical brightener includes：The tertiary fourth of dimethyl maleate, acrylic acid
Ester and (perfluorocyclohexyl) methacrylate, and end-capping reagent, initiator and organic solvent are added in, it is made through copolyreaction.
In the raw material, the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) metering system
The molar ratio of acid esters is 20-50：15-35：10-25.
The molar ratio of the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylate
For 35：25：18.
The end-capping reagent include cyclopentene, additive amount for the dimethyl maleate, tert-butyl acrylate and
The 2-6wt% of (perfluorocyclohexyl) methacrylate monomers gross mass.
The initiator includes benzoyl peroxide, and additive amount is the dimethyl maleate, the tertiary fourth of acrylic acid
The 0.2-0.5wt% of ester and (perfluorocyclohexyl) methacrylate monomers gross mass.
The organic solvent includes N,N-dimethylformamide.
The invention also discloses a kind of methods for preparing the powdery paints optical brightener, include the following steps：
(1) dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylate of formula ratio are taken
Add in abundant mixing in mixer；
(2) controlling reaction temperature is less than 20 DEG C, and adds in the initiator mixing of formula ratio；
(3) organic solvent is then added in, and is progressively warming up to 100 DEG C under nitrogen protection, after stablizing, keeps anti-
Temperature is answered as 100-105 DEG C of progress copolyreaction；
(4) treat after reaction, to reduce temperature of reaction system to 70-80 DEG C, and add in the end-capping reagent of formula ratio into
Row polymerization is handled；
(5) organic solvent described in removed under reduced pressure and unreacted each starting monomer collect colourless viscous fluid at 200 DEG C
Body is cooled to room temperature as colourless solid resin shape optical brightener.
In the step (5), before being additionally included in removed under reduced pressure solvent, entire reaction system is warming up to 180-200 DEG C
Step.
The purposes of powdery paints is used to prepare with optical brightener the invention also discloses the powdery paints.
The powdery paints is polyester -- Epoxy-resin-type powder paint.
Powdery paints optical brightener of the present invention, using dimethyl maleate, tert-butyl acrylate and (perfluor
Cyclohexyl) methacrylate is raw material, through the hydrophobic ternary coexisted with hydrophilic segment in copolyreaction prepared composition minor structure
Copolymer is hydrophobic more regular with hydrophilic radical in entire copolymer as segment main body, copolymer obtained it is hydrophobic with it is hydrophilic
Relative equilibrium, it is more preferable with the compatibility of powdery paints compared with existing conventional propylene acid type optical brightener, it can preferably soak
Base material improves adhesive force, is made that the shock resistance of coating is more excellent, and film-forming is excellent and the levelability of powdery paints is more preferable.
Optical brightener of the present invention carries out sealing end copolymerization using cyclopentene, advantageously forms more regular end group segment so that add lustre to
Agent molecule structure is relatively unified, while reaches slight shift to the function of coating surface, and performance of adding lustre to is apparent, can prepare high glaze
Powdery paints is used；And fluoro raw material improves the water resistance of optical brightener, boiling ability significantly improves.It is of the present invention to add lustre to
Agent further improves the performance of powdery paints, and has widened the application field of powdery paints.
Specific embodiment
Embodiment 1
The raw material for preparing of optical brightener described in the present embodiment includes：
Dimethyl maleate 20mol, tert-butyl acrylate 35mol, (perfluorocyclohexyl) methacrylate
15mol；
Cyclopentene accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylic acid
The 6% of ester monomer gross mass；
Benzoyl peroxide accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methyl
The 0.5% of acrylate monomer gross mass；And excessive N,N-dimethylformamide organic solvent.
The method that powdery paints optical brightener is prepared described in the present embodiment, includes the following steps：
(1) dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylate of formula ratio are taken
Add in abundant mixing in mixer；
(2) mixer is led to chilled water to cool down, 18-20 DEG C of controlling reaction temperature, adds in and match somebody with somebody into above-mentioned mixer
The benzoyl peroxide mixing just measured；
(3) it is solvent then to excessive n,N-Dimethylformamide is added in reaction kettle, and under nitrogen protection progressively
100 DEG C are warming up to, after a period of stabilisation, starts metering pump and the mixed monomer solution in mixer is uniformly instilled into reaction kettle,
When time for adding is 2-4 small, reaction temperature is during which kept as 100-105 DEG C of progress copolyreaction；After mix monomer adds, heat preservation
0.5-1.5h is reacted, facilitates being sufficiently formed for fluoropolymer resin；
(4) treat after reaction, to reduce temperature of reaction system to 70-80 DEG C, and add in the cyclohexene of formula ratio as envelope
Agent is held, and carries out polymerization processing 1-2h at this temperature；
(5) entire reaction system is warming up to 180-200 DEG C, organic solvent described in removed under reduced pressure and unreacted each raw material
Monomer is collected colourless thick liquid at 200 DEG C, is cooled to room temperature as colourless solid resin shape optical brightener.
Embodiment 2
The raw material for preparing of optical brightener described in the present embodiment includes：
Dimethyl maleate 50mol, tert-butyl acrylate 25mol, (perfluorocyclohexyl) methacrylate
10mol；
Cyclopentene accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylic acid
The 2% of ester monomer gross mass；
Benzoyl peroxide accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methyl
The 0.2% of acrylate monomer gross mass；And excessive N,N-dimethylformamide organic solvent.
The present embodiment prepares the method for the powdery paints optical brightener with embodiment 1.
Embodiment 3
The raw material for preparing of optical brightener described in the present embodiment includes：
Dimethyl maleate 35mol, tert-butyl acrylate 25mol, (perfluorocyclohexyl) methacrylate
18mol；
Cyclopentene accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylic acid
The 4% of ester monomer gross mass；
Benzoyl peroxide accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methyl
The 0.3% of acrylate monomer gross mass；And excessive N,N-dimethylformamide organic solvent.
The present embodiment prepares the method for the powdery paints optical brightener with embodiment 1.
Embodiment 4
The raw material for preparing of optical brightener described in the present embodiment includes：
Dimethyl maleate 40mol, tert-butyl acrylate 20mol, (perfluorocyclohexyl) methacrylate
20mol；
Cyclopentene accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylic acid
The 5% of ester monomer gross mass；
Benzoyl peroxide accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methyl
The 0.4% of acrylate monomer gross mass；And
Excessive N,N-dimethylformamide organic solvent.
The present embodiment prepares the method for the powdery paints optical brightener with embodiment 1.
Embodiment 5
The raw material for preparing of optical brightener described in the present embodiment includes：
Dimethyl maleate 50mol, tert-butyl acrylate 15mol, (perfluorocyclohexyl) methacrylate
25mol；
Cyclopentene accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methacrylic acid
The 3% of ester monomer gross mass；
Benzoyl peroxide accounts for the dimethyl maleate, tert-butyl acrylate and (perfluorocyclohexyl) methyl
The 0.25% of acrylate monomer gross mass；And
Excessive N,N-dimethylformamide organic solvent.
The present embodiment prepares the method for the powdery paints optical brightener with embodiment 1.
Application examples 1-5
It is utilized respectively the optical brightener prepared in 1-5 of the embodiment of the present invention and prepares powdery paints, concrete component includes：Take bis-phenol
A type epoxy resin E-1240kg, dicy-curing agent (DYHARD100S) 40kg, barium sulfate filler 35kg, titanium dioxide CR826 face
Expect 35kg, curing accelerator (BASF2-MI) 0.5kg, wetting dispersing agent (THIXATROL ST) 0.5kg, flow promortor aluminium oxide
The optical brightener 1kg prepared in 0.5kg and embodiment 1-5.
Compare application examples
The raw material of powdery paints prepared by this comparative example is identical with application examples 1-5, differs only in, the optical brightener choosing
With 701 acrylic type optical brighteners of existing conventional powder coatings.
Experimental example
1st, optical brightener performance detection
Performance detection is carried out to the optical brightener being prepared in above-described embodiment 1-5 according to existing conventional method, and is recorded
It see the table below 1.
1 optical brightener performance detection of table
| Number | Appearance | Softening point/DEG C | Tg/℃ | Weight average molecular weight |
| Embodiment 1 | Light yellow clear particle | 110-115 | 50-55 | 12000-14000 |
| Embodiment 2 | Light yellow clear particle | 110-115 | 50-55 | 12000-14000 |
| Embodiment 3 | Water white transparency particle | 115-120 | 55-60 | 14000-16000 |
| Embodiment 4 | Water white transparency particle | 120-125 | 60-65 | 16000-18000 |
| Embodiment 5 | Water white transparency particle | 125-128 | 65-70 | 18000-20000 |
As it can be seen that optical brightener performance of the present invention is stable, especially glass transition temperature and softening point is higher, the optical brightener
Performance further improve.
2nd, performance powder coating detects
Application examples 1-5 is taken respectively and compares the raw material mixing of powdery paints described in application examples, and is divided with screw extruder
Don't push goes out, tabletting, broken, then sheet stock pulverizes and sieves, powdery paints is made.Powdery paints using electrostatic gun be sprayed on through
On metallic plate after surface granosealing, cure through 200 DEG C/10-15min, ready-made model is then put into deionized water
Beaker center pillar 2h, then various performance detections are carried out, it is recorded in table 2.
According to Qualicoat 12thThe standard method of test of d carries out water boiling resistance test, tool to coating obtained by above-mentioned each sample
Body is：Coating sample is placed in the deionized water seethed with excitement at 100 DEG C and is boiled, selects to take out coating sample after the boiling different time
This, is cooled to room temperature, tapes up on surface with one, it is ensured that the air bubble on its surface no more than after 2, one minute with
45° angle does not have any defect or stripping after rapidly and evenly drawing adhesive tape, and color does not have significant change.Each coating it is water-fast
It is as shown in table 2 to boil results of property.
2 performance powder coating testing result of table
Upper table detection data show that the hydrophobic and hydrophilicity of powdery paints optical brightener of the present invention is more uniform,
Hydrophobic and hydrophilic relative equilibrium, it is preferable with the compatibility of powdery paints, it can preferably soak base material, improve the same of adhesive force
When, reach slight shift to the function of coating surface, which can prepare high glaze powder coating, and performance of adding lustre to is apparent,
Film-forming is excellent simultaneously and the good leveling property of powdery paints；And fluoro raw material improves the water resistance of optical brightener, boiling
Ability significantly improves.
Obviously, the above embodiments are merely examples for clarifying the description, and is not intended to 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 the obvious variation thus extended out or
Among changing still in the protection domain of the invention.
Claims (5)
- A kind of 1. polyester -- Epoxy-resin-type powder paint optical brightener, which is characterized in that mainly by acrylate and butenoic acid Ester is made of raw material through copolyreaction, and the raw material composition of the optical brightener includes：Dimethyl maleate, tert-butyl acrylate And（Perfluorocyclohexyl）Methacrylate, and add in that cyclopentene is end-capping reagent, benzoyl peroxide is initiator and N, N- Dimethylformamide is organic solvent, is made through copolyreaction；In the raw material, the dimethyl maleate, acrylic acid The tert-butyl ester and（Perfluorocyclohexyl）The molar ratio of methacrylate is 20-50：15-35：10-25；The end-capping reagent adds Dosage for the dimethyl maleate, tert-butyl acrylate and（Perfluorocyclohexyl）Methacrylate monomers gross mass 2-6wt%；The additive amount of the initiator for the dimethyl maleate, tert-butyl acrylate and（Perfluor hexamethylene Base）The 0.2-0.5wt% of methacrylate monomers gross mass.
- 2. polyester according to claim 1 -- Epoxy-resin-type powder paint optical brightener, which is characterized in that the suitable fourth Enedioic acid dimethyl ester, tert-butyl acrylate and（Perfluorocyclohexyl）The molar ratio of methacrylate is 35：25：18.
- 3. a kind of prepare claim 1-2 any one of them polyester -- the method for Epoxy-resin-type powder paint optical brightener, It is characterised in that it includes following steps：（1）Take the dimethyl maleate of formula ratio, tert-butyl acrylate and（Perfluorocyclohexyl）Methacrylate adds in Abundant mixing in mixer；（2）Controlling reaction temperature is less than 20 DEG C, and adds in the initiator mixing of formula ratio；（3）The organic solvent is then added in, and is progressively warming up to 100 DEG C under nitrogen protection, after stablizing, keeps reaction temperature It spends for 100-105 DEG C of progress copolyreaction；（4）It treats after reaction, to reduce temperature of reaction system to 70-80 DEG C, and the end-capping reagent for adding in formula ratio is gathered Conjunction is handled；（5）Organic solvent described in removed under reduced pressure and unreacted each starting monomer collect colourless thick liquid at 200 DEG C, cold But it is colourless solid resin shape optical brightener to room temperature.
- 4. the method according to claim 3 for preparing the optical brightener, which is characterized in that the step（5）In, it further includes Before removed under reduced pressure solvent, the step of entire reaction system is warming up to 180-200 DEG C.
- 5. claim 1-2 any one of them polyester -- Epoxy-resin-type powder paint is used to prepare powdery paints with optical brightener Purposes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610363870.4A CN105949859B (en) | 2016-05-23 | 2016-05-23 | A kind of powdery paints optical brightener and preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610363870.4A CN105949859B (en) | 2016-05-23 | 2016-05-23 | A kind of powdery paints optical brightener and preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105949859A CN105949859A (en) | 2016-09-21 |
| CN105949859B true CN105949859B (en) | 2018-06-05 |
Family
ID=56910019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610363870.4A Active CN105949859B (en) | 2016-05-23 | 2016-05-23 | A kind of powdery paints optical brightener and preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105949859B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107573822A (en) * | 2017-10-30 | 2018-01-12 | 惠州市华昱美实业有限公司 | A kind of powdery paints and its preparation technology |
| CN107793822A (en) * | 2017-10-31 | 2018-03-13 | 山东瑞丰高分子材料股份有限公司 | Powdery paints levelling agent and preparation method thereof |
| CN109401392B (en) * | 2018-11-03 | 2021-01-05 | 宁波维楷化学有限公司 | Multifunctional leveling agent for powder coating |
| CN115746313B (en) * | 2022-11-10 | 2024-02-06 | 擎天材料科技有限公司 | Polyester resin, powder coating and preparation method and application thereof |
| CN116120799A (en) * | 2022-12-26 | 2023-05-16 | 合肥杏花印务股份有限公司 | High-gloss offset printing gloss oil |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101260271B (en) * | 2008-04-14 | 2010-06-09 | 佛山市顺德区广业化工实业有限公司 | Transparent cover light powder paint composition and preparation method thereof |
| CN103045000A (en) * | 2012-12-17 | 2013-04-17 | 天津翔盛粉末涂料有限公司 | Special reactive type high-activity flatting agent for powder coating and preparation method thereof |
| CN103965676B (en) * | 2014-04-09 | 2015-06-03 | 天津翔盛粉末涂料有限公司 | Special reactive type high-activity leveling agent for epoxy powder coatings as well as preparation method and application of leveling agent |
| CN105111362B (en) * | 2015-09-14 | 2018-05-11 | 天津翔盛粉末涂料有限公司 | A kind of powdery paints heavy duty detergent minute surface levelling agent and preparation method and application |
-
2016
- 2016-05-23 CN CN201610363870.4A patent/CN105949859B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105949859A (en) | 2016-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105949859B (en) | A kind of powdery paints optical brightener and preparation method and application | |
| CN105061665B (en) | A kind of hydroxy polyacrylate lotion and preparation method and application | |
| CN108864359A (en) | A kind of preparation method of high performance water-soluble high solid low viscosity acrylic resin | |
| CN102134296B (en) | Fluosilicic modification water-soluble acrylic resin dispersion and uses thereof | |
| WO1995009890A1 (en) | Polymeric surfactant and latex made therefrom | |
| CN103540217B (en) | The double-component aqueous car paint of acrylate resin that a kind of aziridine is crosslinked and its preparation method | |
| KR20160082577A (en) | Eco-friendly water-based acrylic resin with high gloss, preparation method thereof and paint comprising the same | |
| CN104031516A (en) | Water-based glass winebottle baking varnish and preparation method thereof | |
| CN1158348A (en) | Aqueous coating compositions | |
| CA1068429A (en) | Process for unsaturated acetoacetate copolymers in aqueous dispersion | |
| CN110818826B (en) | Organic silicon-fluorine flatting agent and preparation process thereof | |
| KR101841356B1 (en) | Vinyl chloride-vinyl acetate copolymer and preparation method thereof | |
| EP3472250B1 (en) | Coating composition with improved liquid stain repellency | |
| EP1944344B1 (en) | Resin composition for plastic coating and plastic coating using the same | |
| US4164488A (en) | Aqueous thermosetting acrylic enamel | |
| CN105884962B (en) | A kind of lacquer lotion and using the lotion as the lacquer of film forming matter | |
| CN113563503A (en) | Preparation method of environment-friendly water-resistant yellowing-resistant copolymer emulsion | |
| CN104893509A (en) | Photocuring paint for wood and preparation method thereof | |
| KR20190072358A (en) | Aqueous acrylic emulsion resin and method for preparing the same | |
| CN110938369A (en) | Anti-cracking UV spraying bright white finish and preparation method thereof | |
| CN114929815B (en) | Wood coating formulations | |
| TWI719113B (en) | Aqueous dispersion, its manufacturing method, water-based paint and coated articles | |
| CN105038486A (en) | Environmental-friendly epoxy modified acrylic based emulsion anti-rust coating | |
| CN104710577B (en) | A kind of rostone manufacturing rostone hydroxy acrylate emulsion, preparation method and make | |
| JPS5819303A (en) | Synthetic resin aqueous dispersion, manufacture and use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Luster-enhancing agent for powder coating as well as preparation method and application of luster-enhancing agent Effective date of registration: 20181128 Granted publication date: 20180605 Pledgee: Bank of China Limited Huangshan Branch Pledgor: HUANGSHAN HUAHUI TECHNOLOGY Co.,Ltd. Registration number: 2018340000680 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20191209 Granted publication date: 20180605 Pledgee: Bank of China Limited Huangshan Branch Pledgor: HUANGSHAN HUAHUI TECHNOLOGY Co.,Ltd. Registration number: 2018340000680 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Luster-enhancing agent for powder coating as well as preparation method and application of luster-enhancing agent Effective date of registration: 20191218 Granted publication date: 20180605 Pledgee: Bank of China Limited Huangshan Branch Pledgor: HUANGSHAN HUAHUI TECHNOLOGY Co.,Ltd. Registration number: Y2019980001092 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20201223 Granted publication date: 20180605 Pledgee: Bank of China Limited Huangshan Branch Pledgor: HUANGSHAN HUAHUI TECHNOLOGY Co.,Ltd. Registration number: Y2019980001092 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A brightener for powder coatings and its preparation method and Application Effective date of registration: 20201223 Granted publication date: 20180605 Pledgee: Bank of China Limited Huangshan Branch Pledgor: HUANGSHAN HUAHUI TECHNOLOGY Co.,Ltd. Registration number: Y2020990001490 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230411 Granted publication date: 20180605 Pledgee: Bank of China Limited Huangshan Branch Pledgor: HUANGSHAN HUAHUI TECHNOLOGY Co.,Ltd. Registration number: Y2020990001490 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A brightener for powder coatings and its preparation method and application Effective date of registration: 20230424 Granted publication date: 20180605 Pledgee: Bank of China Limited Huangshan Branch Pledgor: HUANGSHAN HUAHUI TECHNOLOGY Co.,Ltd. Registration number: Y2023980039042 |