CN106118173B - Hydrophilic antifogging coating composition of photo-thermal dual curable and preparation method thereof - Google Patents
Hydrophilic antifogging coating composition of photo-thermal dual curable and preparation method thereof Download PDFInfo
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- CN106118173B CN106118173B CN201610607724.1A CN201610607724A CN106118173B CN 106118173 B CN106118173 B CN 106118173B CN 201610607724 A CN201610607724 A CN 201610607724A CN 106118173 B CN106118173 B CN 106118173B
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- hydrophilic
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- coating composition
- antifogging coating
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- 230000009977 dual effect Effects 0.000 title claims abstract description 25
- 239000008199 coating composition Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 230000010148 water-pollination Effects 0.000 claims abstract description 9
- 239000004094 surface-active agent Substances 0.000 claims abstract description 7
- 239000006184 cosolvent Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- -1 acrylate ester Chemical class 0.000 claims description 13
- 239000004925 Acrylic resin Substances 0.000 claims description 11
- 229920000178 Acrylic resin Polymers 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006266 etherification reaction Methods 0.000 claims description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 239000004640 Melamine resin Substances 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- OIHZYOFSMBHUPD-UHFFFAOYSA-N 2,6-dihydroxy-2,6-dimethyl-3,5-diphenylheptan-4-one Chemical group CC(C)(O)C(C(=O)C(c1ccccc1)C(C)(C)O)c1ccccc1 OIHZYOFSMBHUPD-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- PYIFORKDZLZXNS-UHFFFAOYSA-N [K].C(C(=C)C)(=O)O.CCCS(=O)(=O)O Chemical group [K].C(C(=C)C)(=O)O.CCCS(=O)(=O)O PYIFORKDZLZXNS-UHFFFAOYSA-N 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229920000151 polyglycol Polymers 0.000 claims description 2
- 239000010695 polyglycol Substances 0.000 claims description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- SBVKVAIECGDBTC-UHFFFAOYSA-N 4-hydroxy-2-methylidenebutanamide Chemical compound NC(=O)C(=C)CCO SBVKVAIECGDBTC-UHFFFAOYSA-N 0.000 claims 1
- 229920001807 Urea-formaldehyde Polymers 0.000 claims 1
- TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 claims 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 34
- 239000011248 coating agent Substances 0.000 abstract description 33
- 238000001723 curing Methods 0.000 abstract description 12
- 238000013007 heat curing Methods 0.000 abstract description 12
- 238000000016 photochemical curing Methods 0.000 abstract description 10
- 239000000758 substrate Substances 0.000 abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 7
- 239000000853 adhesive Substances 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- 239000004033 plastic Substances 0.000 abstract 2
- 230000000052 comparative effect Effects 0.000 description 21
- 230000000694 effects Effects 0.000 description 8
- 230000002209 hydrophobic effect Effects 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 230000002045 lasting effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920001427 mPEG Polymers 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229940059939 kayexalate Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000002035 prolonged effect 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
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 210000002268 wool Anatomy 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses hydrophilic antifogging coating compositions of a kind of photo-thermal dual curable and preparation method thereof；The composition includes 32~50 parts of hydrophily heat reactive resin, and 10~15 parts of waterborne curing agent, 10~20 parts of the acrylate monomer of hydroxyl, 10~20 parts of polymerisable surfactant, 0.5~1 part of photoinitiator；5~10 parts of cosolvent；300~500 parts of water.The hydrophilic antifogging coating of photo-thermal dual curable provided by the invention can be applied to plastic rubber substrate surface, after first passing through heat cure, using photocuring, continue anti-fog properties and wear-resisting property with excellent, there is good adhesive force to plastic rubber substrate simultaneously, it can be widely used in antifogging vehicle window pad pasting, automobile antifogging headlight, bathroom mirror etc., have a good application prospect.
Description
Technical field
The present invention relates to hydrophilic antifogging coating compositions of a kind of photo-thermal dual curable and preparation method thereof, and it is double to belong to photo-thermal
The coating material solidified field of weight.
Background technique
Vapor in air will condense into small drop and mist formation when temperature is lower than dew point.It is this undesirable
Influence frequently occurs in window, bathroom mirror, glasses, swimming and Lunettes, windshield, optical instrument camera lens, car light, refers to
Showing lamp, agricultural film etc., these live on the transparent material being closely related with us.Transparent material surface water droplet atomization as a result, not only
Light transmittance decline influences vision, generates harm sometimes, such as when droplet condenses in such as infrared optics microscope rigorous analysis
When on the lens surface of instrument, the accuracy of analysis can be reduced.And when droplet condenses on solar battery light-transmitting plate, it causes
Make the reduction of solar absorption efficiency, so that being unfavorable for solar cell device gives full play to due effect.
In order to solve these problems, can generally hydrophobic or hydrophilic treated be carried out to material surface.Hydrophobic common perfluorinated resin
Class, one side price is higher, and on the other hand the resinoid is generally softer, wears no resistance, while its hydrophobic property also leads to its table
Face easily adsorbs greasy dirt and dust, the effect not reached requirement instead.And organic hydrophilic coating price itself is inexpensively, it can also
Its wearability is improved by some modifications.Using organic hydrophilic coating compared to hydrophobic coating processing method not only construction party
Just, and it is cheap.
It is concentrated mainly on super hydrophilic research both at home and abroad now, as coating surface introducing can form the group such as carboxylic of hydrogen bond
Base, amino, sulfydryl, hydroxyl or some ionic groups: carboxylate radical, sulfonate radical, ammonium root, phosphate radical etc., when these groups of introducing
Or when ion, the surface of coating reaches super hydrophilic state, sprawls after moisture condensation in substrate surface height, forms one layer
Even moisture film eliminates tiny drops of water and achievees the purpose that antifog to the diffusing reflection of light.Super hydrophilic approach master is prepared at present
If passing through physical blending, Chemical modification, chemical bond connection.Anti-fog coating currently on the market continue anti-fog performance with it is resistance to
Mill performance can not balance, and after a period of use, anti-fog performance just declines obviously.
Chinese patent CN 102795791A discloses a kind of wear-resisting super hydrophilic antireflecting coating, and the coating by depositing repeatedly
Diallyl dimethyl ammoniumchloride and kayexalate prepare 5~20 layers of double-layer structure, then poly- by deposition repeatedly
Diallyldimethylammonium chloride and the SiO for being 10~40nm containing partial size2The suspension of nano spherical particle prepares 3~8 layers
Double-layer structure, then 100~300s system is quenched by 100~140 DEG C of hydro-thermal process and in 600~800 DEG C of Muffle furnace
Coating needed for obtaining.Although coating made from this method can reach the high rigidity of 5H and water contact angle also very little, step is complicated,
Lasting anti-fog properties general, energy consumption is high, only has the user of special high request suitable performance.
Domestic patent CN102086348A discloses a kind of preparation side of urethane cures acrylate anti-fog coating
Method, the coating is by hydrophilic acrylic resin, enclosed type polyethers isocyanate curing agent and catalyst dibutyltin dilaurylate
Composition.The coating hardness is greater than 2H, and wear-resisting property is good, but lasting anti-fog performance is general, and solidification process needs the time longer, and needs
Stage curing (50~120 DEG C), the process is more complicated.
To overcome traditional anti-fog coating on the market to continue the contradiction of anti-fog performance and wear-resisting property, the present invention discloses a kind of light
The hydrophilic antifogging coating of hot dual cure.The coating passes through heat cure first, uses photocuring, the coating after solidification, parent later
Aqueous splendid and lasting anti-fog performance is outstanding, while will not lose wear-resisting property, therefore overcome the one of anti-fog coating on the market
A little drawbacks are very suitable to do the field that vehicle window, bathroom mirror etc. have antifog requirement.
Summary of the invention
For the defects in the prior art, the object of the present invention is to provide a kind of hydrophilic antifogging coating of photo-thermal dual curable
Composition and preparation method thereof.
The present invention is achieved by the following technical solutions:
In a first aspect, the present invention provides a kind of hydrophilic antifogging coating compositions of photo-thermal dual curable comprising by weight
Measure the following component of number meter:
Hydrophily heat reactive resin adding proportion is 32~50 parts, and the effect of the part, which is to provide, in entire formula continues
Anti-fog performance, ratio is too low when being lower than 32 parts, and it is undesirable to continue anti-fog performance；Higher than 50 parts hydrophilic resins are too many, lead to hardness
Requirement is unable to reach with wear-resisting property.
The adding proportion of waterborne curing agent is 10~15 parts, and the effect of the component in formula is and hydrophilic hydroxyl groups acrylic acid
Resin cross-linking reaction, additive amount have excessive Hydroxylated acrylic resin to have neither part nor lot in reaction, lead to coating crosslink density less than 10 parts
Decline, hardness decline, it is poor to continue anti-fog performance；And it is excessive higher than 15 parts of adding proportions, cause crosslink density excessive, hydrophily portion
Divide and be not easy to move to surface, anti-fog performance is caused to decline.
The adding proportion of the acrylate monomer of hydroxyl is 10~20 parts, additive amount and polymerisable surfactant one
It causes, plays intermediate link part, add the excessive mechanical performance for influencing coating, addition influences initial anti-fog performance very little.
Preferably, the hydrophily heat reactive resin is hydrophilic hydroxy group acroleic acid resin.
Preferably, the hydrophilic hydroxy group acroleic acid resin is by monomethyl polyethylene glycol acrylate ester, propylene
Monomer shown in sour hydroxyl ethyl ester, acrylic acid and formula (I) is prepared by the method for solution-type free radical polymerization, wherein shown in formula (I)
Monomer, monomethyl polyethylene glycol acrylate ester, hydroxy-ethyl acrylate, acrylic acid weight percent be respectively 15~25%,
25~35%, 40~50% and 3~6%,
Preferably, the preparation method of the hydrophilic hydroxy group acrylic resin specifically comprises the following steps:
By monomer and initiator shown in monomethyl polyethylene glycol acrylate ester, hydroxy-ethyl acrylate, acrylic acid, formula (I)
20%, after mixing is respectively taken, is reacted 0.5 hour at 80~85 DEG C, then remaining poly glycol monomethyl ether third is added in 2 hours
Olefin(e) acid ester, hydroxy-ethyl acrylate, acrylic acid, monomer and initiator shown in formula (I), the reaction was continued, obtains the hydrophily hydroxyl
Base acrylic resin.
The hydroxyl of the hydrophilic hydroxy group acroleic acid resin prepared using the above method is in side chain, it is easy to and amino resins
The alkoxy grp of curing agent occurs condensation reaction and forms the fine and close hydrophobic network of crosslinking.It can repel equally in the hydrophilic of side chain
Property moiety aggregation is in film coated surface, therefore the good hydrophilic property on surface, and the network structure partially hydrophobic inside film is good.To lead
It causes film that there is excellent hydrophilicity, the condensation vapor in air can be made to be formed on its surface moisture film rather than water droplet, have
There is good anti-fog performance.In addition there is enough hydrophobic networks inside film, water or vapor will not be caused to fall painting film bubble,
So having protracted hydrophilicity good, has and continue anti-fog performance.
Preferably, the waterborne curing agent includes the melamine resin of methanol etherification, methanol etherification
Benzoguanamine resin, methanol etherification Lauxite one or more of combinations.Further, the waterborne curing agent
For the melamine resin of methanol etherification, because of its good water solubility, and crosslink density is high, and hardness wear-resisting property is excellent.
Preferably, the acrylate monomer of the hydroxyl is hydroxyethyl methacrylate, hydroxylethyl acyl
Amine, one or more of combinations of hydroxypropyl acrylate.With waterborne curing agent heat cure can occur for the hydroxyl in such component,
And the double bond in structure can participate in photocuring reaction, be the bridging component in photo-thermal dual curable.
Preferably, the polymerisable surfactant is selected from 3- propyl sulfonic acid methacrylic acid potassium, 2- acryloyl
Amine -2- methyl propane sulfonic acid, one or more of combinations of allyloxy Nonylphenoxy propyl alcohol polyoxyethylene ether ammonium sulfate, such
Component can substantially reduce hydrophilic angle, and may participate in photocuring reaction, have splendid lasting hydrophilic effect, adding proportion with
The acrylate monomer of hydroxyl is consistent.
Preferably, the photoinitiator is 2- hydroxy-2-methyl -1- phenyl -1- propyl ketone；1- [4- (2- hydroxyl second
Oxygroup)-phenylene] -2- hydroxyl -2 ', 2 '-dimethyl ethyl ketones；1- hydroxycyclohexyl phenyl ketone；2- methyl-1-(4- methyl mercapto
At least one of phenyl) -2- morpholine -1- acetone.
Preferably, the cosolvent is propandiol butyl ether, butyl glycol ether, propylene glycol methyl ether acetate, alcohol ester-
12, at least one of propylene glycol phenylate, benzyl alcohol.
Second aspect, the present invention provides a kind of systems of the hydrophilic antifogging coating composition of photo-thermal dual curable as the aforementioned
Preparation Method comprising following steps:
Accurately weigh each component, by hydrophily heat reactive resin, waterborne curing agent, hydroxyl acrylate monomer, can
Polymeric surfactant and deionized water mix at room temperature, add photoinitiator and auxiliary agent, and mixing obtains.
The application method of the hydrophilic antifogging coating composition of a kind of photo-thermal dual curable of the invention are as follows: by the painting
Feed composition is coated in PET base material, through 130 DEG C, the heat cure of 2min, 500mJ/cm2UV solidify dual cure.
Compared with prior art, the present invention have it is following the utility model has the advantages that
If anti-fog coating protracted hydrophilicity on the market can be excellent, wear-resisting property just not can guarantee；It is wear-resisting in hardness on the contrary
While excellent, persistently anti-fog effect is general.And the present invention, on the basis of heat cure, further progress photocuring passes through increasing
Add the crosslink density of coating, so that wear-resisting and hardness effectively enhances, while continuing anti-fog performance and also greatly improving, because long-term
In water environment, high crosslinking degree can hinder hydrophilic component reduction soluble in water anti-fog properties, and furthermore photocureable coating is due to solidification
When can generate contraction, by adding heat reactive resin in component, the contraction of system can be can be greatly reduced in adhesive force decline,
Improve adhesive force.
Specific embodiment
The present invention is described in detail combined with specific embodiments below.Following embodiment will be helpful to the technology of this field
Personnel further understand the present invention, but the invention is not limited in any way.It should be pointed out that the ordinary skill of this field
For personnel, without departing from the inventive concept of the premise, various modifications and improvements can be made.These belong to the present invention
Protection scope.
Examples 1 to 5 in the present invention, comparative example 1~3, comparative example 4~6 and comparative example 7~8 formula be listed in table respectively
1,2 table 3 of table and table 4, hydrophilic hydroxy group acroleic acid resin described in table are prepared by the following method to obtain:
Synthesis example 1The synthesis of hydrophilic hydroxy group acrylic resin A
Equipped with mechanical stirring, thermometer, nitrogen gatherer 100 milliliters of four-hole bottles in, be added glycol monoethyl ether
(10 grams), first plus 20% monomer, initiator ammonium persulfate (0.069 gram) and glycol monoethyl ether (45 grams) mixture,
Temperature is increased to 80~85 DEG C, is reacted 0.5 hour.Then remaining monomer, initiator and glycol monoethyl ether are added dropwise in 2 hours
Mixture, after dripping, after the reaction was continued 3 hours, be cooled to room temperature and obtain pale yellow viscous liquid.Then with n-hexane into
Row precipitating, then be dried in vacuo through 50 degree and obtain within 12 hours gained hydrophilic hydroxy group acrylic resin A.The monomer mixture includes
Monomer I (3.2 grams), 550 acrylate of methoxy poly (ethylene glycol) (MPEG550A, 4.0 grams), HEA (6.0 grams) and AA (0.55
Gram).
Synthesis example 2The synthesis of hydrophilic hydroxy group acrylic resin B
Equipped with mechanical stirring, thermometer, nitrogen gatherer 100 milliliters of four-hole bottles in, be added glycol monoethyl ether
The mixing of 20% monomer, initiator ammonium persulfate (0.069 gram) and glycol monoethyl ether (45 grams) is first added in (10 grams)
Object increases temperature to 80~85 DEG C, reacts 0.5 hour.Then remaining monomer, initiator and ethylene glycol list are added dropwise in 2 hours
The mixture of methyl ether after dripping, after the reaction was continued 3 hours, is cooled to room temperature and obtains pale yellow viscous liquid.Then with just oneself
Alkane is precipitated, then is dried in vacuo through 50 DEG C and is obtained within 12 hours gained hydrophilic hydroxy group acrylic resin B.The monomer mixture
Including 600 acrylate of methoxy poly (ethylene glycol) (MPEG600A, 4.0 grams), HEA (6.0 grams), AA (0.55 gram).
Examples 1 to 5
Examples 1 to 5 is related to a kind of hydrophilic antifogging coating composition of photo-thermal dual curable, including component shown in table 1
And parts by weight.
Using PET as substrate, coating (30% contains admittedly) is coated on its surface with No. 10 line stick, is put into 130 DEG C of baking ovens
2min solidifies by UV, energy 500mJ/cm later2。
Comparative example 1~8
Comparative example 1~3 is related to a kind of hydrophilic antifogging coating composition of heat cure, including component shown in table 2 and weight
Number.
Using PET as substrate, coating (30% contains admittedly) is coated on its surface with No. 10 line stick, is put into 180 DEG C of baking ovens
2min。
Comparative example 4~6 is related to a kind of hydrophilic antifogging coating composition of photocuring, including component shown in table 3 and weight
Number.
Using PET as substrate, coating (30% contains admittedly) is coated on its surface with No. 10 line stick, is put into 70 DEG C of baking ovens
4min solidifies by UV, energy 500mJ/cm later2。
Comparative example 7 is related to a kind of hydrophilic antifogging coating composition of photo-thermal dual curable, including component shown in table 4 and again
Measure number.
Using PET as substrate, coating (30% contains admittedly) is coated on its surface with No. 10 line stick, is put into 130 DEG C of baking ovens
2min, later without photocuring.
Comparative example 8 is related to a kind of hydrophilic antifogging coating composition of photo-thermal dual curable, including component shown in table 4 and again
Measure number.
Using PET as substrate, coating (30% contains admittedly) is coated on its surface with No. 10 line stick, is put into 70 DEG C of baking ovens
4min solidifies by UV, energy 500mJ/cm later2, this technique do not carry out heat cure, the conditioned response of 70 DEG C of baking oven 4min
Minimum temperature needed for temperature is lower than heat cure.
Each component and its parts by weight in 1 Examples 1 to 5 of table
Each component and its parts by weight in 2 comparative example 1~3 of table
Each component and its parts by weight in 3 comparative example 4~6 of table
Each component and its parts by weight in 4 comparative example 7~8 of table
Performance detection
Performance detection is carried out to coating made from Examples 1 to 5 and comparative example 1~8 respectively, measures the attachment of coating
Power, pencil hardness, wearability, initial stage water contact angle and sustained water contact angle performance.
Specific performance detection project and corresponding method are as follows:
One, adhesive force
Using baige method, specimen page adhesive force is tested with 3M Pressure sensitive adhesive tape.
Appraisal procedure: 5B- scribing edge is smooth, at the edge and intersection of scribing line without peeling paint；
4B- has the peeling paint of small pieces in the intersection of scribing line, and the gross area that falls off is less than 5%；
3B- has the peeling paint of small pieces at the edge and intersection of scribing line, and fall off the gross area 5~15% it
Between；
2B- has sheet of peeling paint at the edge and intersection of scribing line, and fall off the gross area 15~35% it
Between；
1B- has sheet of peeling paint at the edge and intersection of scribing line, and fall off the gross area 35~65% it
Between；
0B- has sheet of peeling paint at the edge and intersection of scribing line, and the gross area that falls off is greater than 65%.
Two, pencil hardness
Referring to standard GB/T/T6739 " hardness of paint film pencil measuring method ".
Three, wear-resisting property
Using 0000# steel wool, 300g power, one is denoted as once back and forth, and the number scratched occurs in recording surface.
Appraisal procedure: after the friction of certain number, whether observation coating has scratch, is resistant to when recording without scratch
Most Rubbing numbers.
Four, initial stage hydrophilic angle
4 μ L deionized waters are dripped in the specimen surface being cured, are measured within the scope of 20~25 DEG C with contact angle tester.
Five, continue hydrophilic angle
The sample being cured is put into deionized water and impregnates 100h, is measured after drying with contact angle measurement.
By the test result of Examples 1 to 5 and comparative example 1~8, including attachment, pencil hardness, wear-resisting, initial stage hydrophilic angle
Persistently hydrophilic angle is summarized as follows table 3.
5 embodiment and comparative example test result of table
As shown in Table 5, the hardness of embodiment is higher than comparative example, because the embodiment of the present invention uses dual cure,
Further photocuring on the basis of heat cure, crosslink density are significantly larger than individual curing mode, and performance is embodied in hardness and resistance to
On mill, more single curing mode has promotion；In addition, in comparative example, the hardness of photocuring system and wear-resisting micro- it is better than heat cure
System, because its crosslink density is higher than heat cure；Comparative example 7 and 8 and example 1 group point are consistent, but curing mode is different, right
Ratio 7 is only with heat cure, and comparative example 8 is only with photocuring, therefore crosslink density is far away from dual cure, aspect of performance hardness
It is wear-resisting not reach requirement, and protracted hydrophilicity can be also good without embodiment 1.It is close in the early stage from the point of view of Comprehensive Correlation example and embodiment
Water aspect of performance, comparative example and embodiment difference are not that too greatly, because of the addition of surface reactive material, can reduce parent well
Water angle plays excellent anti-fog effect, but at persistently hydrophilic aspect, the hydrophilic angle of embodiment will be lower than comparative example, because
Polymerisable surfactant has been connected in main structure by cross-linking reaction, in addition the crosslink density of superelevation, cause even across
Prolonged water immersion will not steep；And comparative example is impregnated by long-time, hydrophilic angle can increase significantly, continue anti-fog properties
Can be poor, effect of the invention is not achieved in comprehensive performance.
Specific embodiments of the present invention are described above.It is to be appreciated that the invention is not limited to above-mentioned
Particular implementation, those skilled in the art can make various deformations or amendments within the scope of the claims, this not shadow
Ring substantive content of the invention.
Claims (8)
1. a kind of hydrophilic antifogging coating composition of photo-thermal dual curable, which is characterized in that as follows including according to parts by weight
Component:
The hydrophily heat reactive resin is hydrophilic hydroxy group acrylic resin；
The hydrophilic hydroxy group acroleic acid resin be by monomethyl polyethylene glycol acrylate ester, hydroxy-ethyl acrylate, acrylic acid and
Monomer shown in formula (I) is prepared by the method for solution-type free radical polymerization, wherein monomer, polyethyleneglycol shown in formula (I)
Methyl ether acetate, hydroxy-ethyl acrylate, acrylic acid weight percent be respectively 15~25%, 25~35%, 40~50%
With 3~6%,
2. the hydrophilic antifogging coating composition of photo-thermal dual curable as described in claim 1, which is characterized in that the hydrophily
The preparation method of Hydroxylated acrylic resin specifically comprises the following steps:
Monomer shown in monomethyl polyethylene glycol acrylate ester, hydroxy-ethyl acrylate, acrylic acid, formula (I) and initiator are respectively taken
20%, after mixing, reacted 0.5 hour at 80~85 DEG C, then remaining poly glycol monomethyl ether acrylic acid is added in 2 hours
Ester, hydroxy-ethyl acrylate, acrylic acid, monomer and initiator shown in formula (I), the reaction was continued, obtains the hydrophilic hydroxy group third
Olefin(e) acid resin.
3. the hydrophilic antifogging coating composition of photo-thermal dual curable as described in claim 1, which is characterized in that described aqueous solid
Agent includes the ureaformaldehyde of the melamine resin of methanol etherification, the benzoguanamine resin of methanol etherification, methanol etherification
The one or more of resin.
4. the hydrophilic antifogging coating composition of photo-thermal dual curable as described in claim 1, which is characterized in that the hydroxyl
Acrylate monomer be hydroxyethyl methacrylate, hydroxyethyl acrylamide, hydroxypropyl acrylate one or more.
5. the hydrophilic antifogging coating composition of photo-thermal dual curable as described in claim 1, which is characterized in that described polymerizable
Surfactant is selected from 3- propyl sulfonic acid methacrylic acid potassium, 2- acrylamide-2-methyl propane sulfonic, allyloxy nonyl benzene oxygen
One or more of base propyl alcohol polyoxyethylene ether ammonium sulfate.
6. the hydrophilic antifogging coating composition of photo-thermal dual curable as described in claim 1, which is characterized in that described light-initiated
Agent is 2- hydroxy-2-methyl -1- phenyl -1- propyl ketone；1- [4- (2- hydroxy ethoxy)-phenylene] -2- hydroxyl -2 ', 2 '-diformazans
Base ethyl ketone；1- hydroxycyclohexyl phenyl ketone；At least one in 2- methyl-1-(4- methyl mercapto phenyl)-2- morpholine-1- acetone
Kind.
7. the hydrophilic antifogging coating composition of photo-thermal dual curable as described in claim 1, which is characterized in that the cosolvent
For at least one in propandiol butyl ether, butyl glycol ether, propylene glycol methyl ether acetate, alcohol ester-12, propylene glycol phenylate, benzyl alcohol
Kind.
8. a kind of system of the hydrophilic antifogging coating composition of the photo-thermal dual curable as described in any one of claim 1~7
Preparation Method, which comprises the steps of:
Accurately weigh each component, by hydrophily heat reactive resin, waterborne curing agent, hydroxyl acrylate monomer, it is polymerizable
Surfactant and deionized water mix at room temperature, add photoinitiator and auxiliary agent, and mixing obtains.
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| JP2019006891A (en) * | 2017-06-23 | 2019-01-17 | トーヨーポリマー株式会社 | Antifogging coating composition and antifogging transparent sheet using the same |
| CN107502044A (en) * | 2017-10-11 | 2017-12-22 | 广东至远实业集团有限公司 | A kind of water-based UV ink of shelf-stable and preparation method thereof |
| CN110908234B (en) * | 2018-08-28 | 2022-08-02 | 深圳光峰科技股份有限公司 | Curing adhesive and projection screen thereof |
| CN109666119B (en) * | 2018-12-25 | 2020-07-24 | 湖南松井新材料股份有限公司 | Water-based antifogging resin, water-based antifogging coating composition and preparation method thereof |
| CN110922843A (en) * | 2019-12-18 | 2020-03-27 | 湖南智涂环保科技有限公司 | Super-hydrophilic coating and preparation method thereof |
| CN113061391B (en) * | 2021-03-29 | 2022-03-18 | 光易科技(无锡)有限公司 | Radiation-cured antifogging coating composition and film and preparation method thereof |
| CN113372800B (en) * | 2021-06-21 | 2022-06-28 | 山西新华防化装备研究院有限公司 | Long-acting antifogging hydrophilic coating liquid and preparation method thereof |
| CN114773987B (en) * | 2022-06-09 | 2023-03-28 | 南通康尔乐复合材料有限公司 | Stretchable UV hardening liquid for automobile decoration film and preparation method of hardened PC (polycarbonate) using stretchable UV hardening liquid |
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