CN115197639B - UVLED (ultraviolet light emitting diode) curing coating for advertisement lamp shade molding - Google Patents
UVLED (ultraviolet light emitting diode) curing coating for advertisement lamp shade molding Download PDFInfo
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- CN115197639B CN115197639B CN202210944656.3A CN202210944656A CN115197639B CN 115197639 B CN115197639 B CN 115197639B CN 202210944656 A CN202210944656 A CN 202210944656A CN 115197639 B CN115197639 B CN 115197639B
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- 238000000576 coating method Methods 0.000 title claims abstract description 53
- 239000011248 coating agent Substances 0.000 title claims abstract description 50
- 238000000465 moulding Methods 0.000 title claims abstract description 26
- 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 claims abstract description 36
- 229920001610 polycaprolactone Polymers 0.000 claims abstract description 31
- 239000004632 polycaprolactone Substances 0.000 claims abstract description 31
- 150000002009 diols Chemical class 0.000 claims abstract description 30
- 239000004814 polyurethane Substances 0.000 claims abstract description 25
- 229920002635 polyurethane Polymers 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000003112 inhibitor Substances 0.000 claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- 239000002518 antifoaming agent Substances 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 239000002270 dispersing agent Substances 0.000 claims abstract description 9
- 239000003999 initiator Substances 0.000 claims abstract description 8
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 6
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 5
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- 239000010703 silicon Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000010521 absorption reaction Methods 0.000 claims description 19
- 238000012544 monitoring process Methods 0.000 claims description 17
- HHFDWBHFYINSFR-UHFFFAOYSA-N 2-sulfanylpropanedioic acid Chemical compound OC(=O)C(S)C(O)=O HHFDWBHFYINSFR-UHFFFAOYSA-N 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 13
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000005259 measurement Methods 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 10
- 230000001678 irradiating effect Effects 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 7
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000005070 sampling Methods 0.000 claims description 4
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- -1 2,4, 6-trimethylbenzoyl phosphorus phenoxide Chemical compound 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 abstract description 16
- 238000004132 cross linking Methods 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 17
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 11
- 239000004926 polymethyl methacrylate Substances 0.000 description 11
- 238000004383 yellowing Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N ethylene glycol diacrylate Substances C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WNTRJGGZNNTIRD-UHFFFAOYSA-N oxido-oxo-(2,4,6-trimethylbenzoyl)phosphanium Chemical compound CC1=CC(C)=C(C(=O)[P+]([O-])=O)C(C)=C1 WNTRJGGZNNTIRD-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
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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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/834—Chemically modified polymers by compounds containing a thiol group
- C08G18/835—Unsaturated polymers modified by compounds containing a thiol group
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2150/00—Compositions for coatings
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
Abstract
The invention provides a UVLED curing coating for molding advertisement lamp covers, which relates to the technical field of coatings, and comprises the following components in parts by weight: 50-80 parts of polycaprolactone diol and bisphenol A epoxy modified polyurethane; 0.1-0.3 part of polymerization inhibitor; 10-20 parts of active monomer; 0.5-1 part of antioxidant; 2-6 parts of gas silicon; 1-5 parts of dispersing agent; 0.1-0.5 part of defoaming agent; 0.1-0.5 part of leveling agent; 3-5 parts of an initiator. When the UVLED curing coating for forming the advertising lamp shade is used, the coating is poured into a mould with a corresponding shape, and then irradiated under an LED with the wavelength of 395nm, so that the crosslinking curing reaction is carried out, and the formed advertising lamp shade can be obtained; the required equipment is simple and convenient, the place requirement is small, and the product specification and pattern can be changed in time, so that the method is suitable for advertising companies of various scales.
Description
Technical Field
The invention relates to the technical field of coatings, in particular to a UVLED curing coating for molding advertisement lampshades.
Background
With the development of LED lamps and the advertising demands of various businesses, the demand of advertising light boxes has increased dramatically. The conventional LED lamp box consists of an LED lamp and a PMMA lamp cover, wherein PMMA is commonly known as organic glass, and has the advantages of good light transmittance, lower price, light weight and high mechanical strength, the production process of the LED lamp box is complicated, the LED lamp box is basically suitable for large-scale production, the product specification and the product style cannot be changed timely along with the requirement, and the flexible and changeable requirement of the advertisement lamp cover cannot be met.
Disclosure of Invention
The invention aims to solve the technical problems that: in order to solve the problem that equipment required by advertisement lamp shade production is complex in the prior art, the invention provides the UVLED curing coating for advertisement lamp shade molding, which has high curing speed and is beneficial to deep curing, the cured coating can meet the performance requirement of the advertisement lamp shade, the required equipment is simple and convenient, the advertisement lamp shade meeting the requirement can be obtained by pouring the coating into a corresponding mold for curing, and the problem that the equipment required by the existing advertisement lamp shade production is complex is solved.
The technical scheme adopted for solving the technical problems is as follows:
the UVLED curing coating for molding the advertising lamp shade comprises the following components in parts by weight:
alternatively, the polycaprolactone diol and bisphenol a epoxy modified polyurethane is prepared according to the following method:
s1: mixing ethoxylated bisphenol A dimethacrylate, a catalyst 1173 and toluene, heating to 40-60 ℃, dropwise adding mercaptoethanol under the protection of inert gas, stirring and irradiating with an LED lamp with the wavelength of 365nm, monitoring the reaction by FTIR measurement, eliminating double bond absorption peak in the reactant, and removing the solvent to obtain a product A;
s2: mixing IPDI and DBTDL catalyst, dropwise adding a product A diluted by butyl acetate and polycaprolactone dihydric alcohol at 50 ℃, reacting, dropwise adding PET3A mixed with polymerization inhibitor BHT, heating to 60-80 ℃ until the content of-NCO groups is below 1%, sampling for infrared test, and monitoring characteristic absorption peaks at 2270cm of-NCO groups until the characteristic absorption peaks completely disappear, thus obtaining a PET3A end-capped product A;
s3: mixing mercaptomalonic acid, the PET3A end-capped product A, toluene and a catalyst 1173, heating to 40-60 ℃, under the protection of inert gas, stirring and irradiating with an LED lamp with the wavelength of 365nm, monitoring the reaction by FTIR measurement, eliminating double bond absorption peak in the reactant, and removing the solvent to obtain a product B;
s4: and mixing the product B, p-toluenesulfonic acid serving as a catalyst, hydroquinone and xylene, heating to 60-80 ℃, dropwise adding PET3A while stirring, monitoring the reaction through FTIR measurement, stopping dropwise adding PET3A after the absorption peak of carboxyl in the reactant disappears, and obtaining the polycaprolactone diol and bisphenol A epoxy modified polyurethane after the reaction is finished.
Optionally, the mass ratio of the catalyst 1173 to the ethoxylated bisphenol a dimethacrylate in step S1 is 1: (1000-1010); the mass ratio of the mercaptoethanol to the ethoxylated bisphenol A dimethacrylate is (5-5.5): (25-26); the molar ratio of mercaptomalonic acid to PET3A end-capped product A in step S3 was 6:1, the volume of toluene was 4 times the sum of the volumes of mercaptomalonic acid and PET3A end-capped product A, and the mass of catalyst 1173 was 1% of the sum of the masses of mercaptomalonic acid and PET3A end-capped product A.
Alternatively, the polycaprolactone diol has a molecular weight of 2000.
Optionally, the polymerization inhibitor is at least one selected from quinone polymerization inhibitors and phenolic polymerization inhibitors.
Optionally, the reactive monomer is at least one selected from 1, 6-ethylene glycol diacrylate, tripropylene glycol diacrylate and ethoxylated pentaerythritol tetraacrylate.
Optionally, the antioxidant is selected from at least one of 1076, 330, 3114.
Optionally, the dispersing agent is a macromolecular dispersing agent; the defoaming agent is an organosilicon defoaming agent or a polyether defoaming agent.
Optionally, the leveling agent is an organosilicon leveling agent;
optionally, the initiator is selected from at least one of 1-hydroxycyclohexyl phenyl ketone, 2,4, 6-trimethylbenzoyl phosphorus dioxide and 4-chlorobenzophenone.
The beneficial effects of the invention are as follows:
the UVLED curing coating for molding the advertising lamp shade provided by the invention takes the polyurethane modified by the polycaprolactone diol and the bisphenol A epoxy as main resin, and the main chain segments of the polyurethane modified by the polycaprolactone diol and the bisphenol A epoxy are modified by the polycaprolactone diol and the bisphenol A epoxy, so that the coating has the advantages of good mechanical property, good weather resistance, small shrinkage, good toughness, 9 functions of functionality, high curing speed and contribution to deep curing; when the UVLED curing coating is used, the coating is poured into a mould with a corresponding shape, and then the LED with the wavelength of 395nm is irradiated for 10-40 s, so that the ultraviolet LED curing coating is subjected to crosslinking curing reaction, and the formed advertising lampshade can be obtained; the thickness of the advertising lampshade formed by the coating can reach 5mm, and the performance of the advertising lampshade can be comparable to that of a PMMA lampshade; the required equipment is simple and convenient, the place requirement is small, and the product specification and pattern can be changed in time so as to meet the requirement of the current eye-catching changeable advertising age, thereby being applicable to advertising companies of various types and scales.
Detailed Description
The present invention will now be described in further detail. The embodiments described below are exemplary and intended to illustrate the invention and should not be construed as limiting the invention, as all other embodiments, based on which a person of ordinary skill in the art would obtain without inventive faculty, are within the scope of the invention.
Along with the development of LED lamps and the increase of advertising demands of merchants, the advertisement lamp shade is required to be flexible and changeable in specification and pattern in order to keep up with the requirement of the eye-catching changeable advertisement era; however, the existing PMMA lamp shade has a relatively fixed production mode and relatively complex equipment, is basically suitable for large-scale production, the product specification and pattern cannot be flexibly changed in real time, and the size, style and color of the product cannot be timely adjusted according to the requirements of clients, so that the PMMA lamp shade is not suitable for advertising companies of various scales.
In order to solve the problem of complex equipment required by advertisement lamp shade production in the prior art, the invention provides a UVLED curing coating for advertisement lamp shade molding, which comprises the following components in parts by weight:
the UVLED curing coating for molding the advertising lamp shade provided by the invention takes the polyurethane modified by the polycaprolactone diol and the bisphenol A epoxy as main resin, and the main chain segments of the polyurethane modified by the polycaprolactone diol and the bisphenol A epoxy are modified by the polycaprolactone diol and the bisphenol A epoxy, so that the coating has the advantages of good mechanical property, good weather resistance, small shrinkage, good toughness, 9 functions of functionality, high curing speed and contribution to deep curing; when the UVLED curing coating is used, the coating is poured into a mould with a corresponding shape, and then the LED with the wavelength of 395nm is irradiated for 10-40 s, so that the ultraviolet LED curing coating is subjected to crosslinking curing reaction, and the formed advertising lampshade can be obtained; the thickness of the advertisement lamp shade formed by the coating can reach 5mm, the performance can be comparable to that of a PMMA lamp shade, and the performance requirement of the advertisement lamp shade is met; the required equipment is simple and convenient, the place requirement is small, and the product specification and pattern can be changed in time so as to meet the requirement of the current eye-catching changeable advertising age, thereby being applicable to advertising companies of various types and scales.
In addition, because the PMMA has low surface hardness and poor scratch resistance, the advertisement lamp shade formed by the UVLED curing coating provided by the invention has higher surface hardness and better scratch resistance compared with the PMMA lamp shade.
The preferred polycaprolactone diol and bisphenol A epoxy modified polyurethane of the present invention is prepared as follows:
s1: mixing ethoxylated bisphenol A dimethacrylate (BPA 4 EODMA), catalyst 1173 and toluene, heating to 40-60 ℃, dropwise adding mercaptoethanol under the protection of inert gas, stirring while irradiating with an LED lamp with a wavelength of 365nm, monitoring the reaction by FTIR measurement, eliminating double bond absorption peak in the reactant, and removing solvent to obtain a product A;
s2: mixing IPDI and DBTDL catalyst, dropwise adding a product A diluted by butyl acetate and polycaprolactone dihydric alcohol at 50 ℃, reacting, dropwise adding PET3A mixed with polymerization inhibitor BHT, heating to 60-80 ℃ until the content of-NCO groups is below 1%, sampling for infrared test, and monitoring characteristic absorption peaks at 2270cm of-NCO groups until the characteristic absorption peaks completely disappear, thus obtaining a PET3A end-capped product A;
s3: mixing mercaptomalonic acid, a PET3A end-capped product A, toluene and a catalyst 1173, heating to 40-60 ℃, under the protection of inert gas, stirring and irradiating with an LED lamp with the wavelength of 365nm, monitoring the reaction by FTIR measurement, eliminating the double bond absorption peak in the reactant, and removing the solvent to obtain a product B;
s4: mixing the product B, p-toluenesulfonic acid serving as a catalyst, hydroquinone and xylene, heating to 60-80 ℃, dropwise adding PET3A while stirring, monitoring the reaction through FTIR measurement, stopping dropwise adding PET3A after the absorption peak of carboxyl in the reactant disappears, and obtaining the polycaprolactone diol and bisphenol A epoxy modified polyurethane after the reaction is finished.
The polyurethane provided by the invention has the main chain segment of polycaprolactone diol and bisphenol A epoxy modified polyurethane, can be rapidly crosslinked and cured under LED illumination when used for coating, has good mechanical property, good weather resistance, small shrinkage and good toughness of a cured paint film, and can be suitable for forming advertising lampshades.
In order to give consideration to the comprehensive performance and the curing speed of the paint film, the mass ratio of the catalyst 1173 to the ethoxylated bisphenol A dimethacrylate in the step S1 is preferably 1: (1000-1010); the mass ratio of the mercaptoethanol to the ethoxylated bisphenol A dimethacrylate is (5-5.5): (25-26); in the step S2, the mass ratio of the DBTDL catalyst to the IPDI is 1: (750-760); in the product A diluted by butyl acetate, the mass concentration of the product A is 20%; the mass of the polymerization inhibitor BHT is 0.1% of the mass of PET 3A; the molar ratio of mercaptomalonic acid to PET3A end-capped product A in step S3 is 6:1, the volume of toluene is 4 times the sum of the volumes of mercaptomalonic acid and PET3A end-capped product A, and the mass of catalyst 1173 is 1% of the sum of the masses of mercaptomalonic acid and PET3A end-capped product A; in the step S4, the mass ratio of the product B to the catalyst p-toluenesulfonic acid to the hydroquinone is 8.03:0.01:0.001, and the volume concentration of the product B in the dimethylbenzene is 0.3g/mL.
Further, the weight average molecular weight of the polycaprolactone diol of the present invention is preferably 2000.
In order to ensure the comprehensive performance of the UVLED curing coating for molding the advertising lamp shade, the polymerization inhibitor is preferably at least one selected from quinone polymerization inhibitor and phenolic polymerization inhibitor; the active monomer is at least one selected from 1, 6-ethylene glycol diacrylate, tripropylene glycol diacrylate and ethoxylated pentaerythritol tetraacrylate; the antioxidant is at least one selected from 1076, 330 and 3114; the dispersing agent is macromolecular dispersing agent; the defoaming agent is an organosilicon defoaming agent or a polyether defoaming agent; the leveling agent is an organosilicon leveling agent.
The initiator is preferably a radical initiator, and further preferably the initiator is at least one selected from the group consisting of 1-hydroxycyclohexylphenyl ketone (CBP), 2,4, 6-trimethylbenzoyl diphenyloxide phosphorus (TPO), 4-chlorobenzophenone (184).
In order that the above-recited objects, features and advantages of the present invention will become more readily apparent, a more particular description of embodiments of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
The polycaprolactone diol and bisphenol a epoxy modified polyurethane of the examples and comparative examples of the present invention were prepared as follows:
s1: adding 50.2g of ethoxylated bisphenol A dimethacrylate (BPA 4 EODMA), 0.05g of catalyst 1173 and 70mL of toluene into a three-hole round-bottomed flask, then raising the temperature of the round-bottomed flask to 50 ℃, dropwise adding 10.4g of mercaptoethanol into the flask under the protection of nitrogen, stirring and irradiating with an LED lamp with the wavelength of 365nm, monitoring the reaction by FTIR measurement, eliminating the double bond absorption peak in the reactant, and removing the solvent by rotary evaporation to obtain a product A;
s2: 30.2g of IPDI and 0.04g of a 0.3% solids DBTDL catalyst were placed in a three-neck flask equipped with a thermometer, an electric stirrer, and a product A diluted with butyl acetate (wherein the mass concentration of the product A is 20%) and a polycaprolactone diol having a molecular weight of 2000 (n (-OH) ratio of polycaprolactone diol to product A is 1:1) were added dropwise with a dropping funnel at 50℃with n (-NCO): n (-OH) =2: 1, continuously monitoring the content of-NCO in the reaction; when the theoretical value is reached, dropwise adding PET3A mixed with a proper amount of polymerization inhibitor BHT, heating to 70 ℃, sampling and carrying out infrared monitoring on characteristic absorption peaks of about 2270cm of the-NCO group when the-NCO group content is below 1%, and obtaining a PET3A end-capped product A when the-NCO group completely disappears;
s3: adding mercaptomalonic acid and PET3A end-capped product A with the molar ratio of 6:1 and toluene with the volume being 4 times of the sum of the mercaptomalonic acid and PET3A end-capped product A, adding a catalyst 1173 with the mass of 1% of the sum of the mercaptomalonic acid and PET3A end-capped product A into a round-bottomed flask, heating to 50 ℃, stirring while irradiating with an LED lamp with the wavelength of 365nm under the protection of nitrogen, monitoring the reaction by FTIR measurement, removing a double bond absorption peak in the reactant, and removing a solvent by rotary evaporation to obtain a product B;
s4: mixing a product B and a proper amount of catalyst p-toluenesulfonic acid, hydroquinone and xylene, wherein the mass ratio of the product B to the catalyst p-toluenesulfonic acid to the hydroquinone is 8.03:0.01:0.001, and the volume concentration of the product B in the xylene is 0.3g/mL; and (3) heating to 70 ℃, dropwise adding PET3A while stirring, monitoring the reaction by FTIR measurement, stopping dropwise adding PET3A after the absorption peak of carboxyl in the reactant disappears, and obtaining the polycaprolactone diol and bisphenol A epoxy modified polyurethane after the reaction is finished.
The leveling agents in the embodiments and the comparative examples are BYK-333, the defoaming agents are BYK-022, the dispersing agent is BYK-163, the antioxidant is 1076, the polymerization inhibitor is BHT, the gas silicon is German Wake H2000, and the initiator is 184.
Example 1
The embodiment provides a UVLED curing coating for molding an advertisement lamp shade, which comprises the following components in parts by weight:
example 2
The embodiment provides a UVLED curing coating for molding an advertisement lamp shade, which comprises the following components in parts by weight:
example 3
The embodiment provides a UVLED curing coating for molding an advertisement lamp shade, which comprises the following components in parts by weight:
example 4
The embodiment provides a UVLED curing coating for molding an advertisement lamp shade, which comprises the following components in parts by weight:
example 5
The embodiment provides a UVLED curing coating for molding an advertisement lamp shade, which comprises the following components in parts by weight:
example 6
The embodiment provides a UVLED curing coating for molding an advertisement lamp shade, which comprises the following components in parts by weight:
example 7
The embodiment provides a UVLED curing coating for molding an advertisement lamp shade, which comprises the following components in parts by weight:
comparative example 1
The comparative example provides a UVLED curing coating, which comprises the following components in parts by weight:
the commercially available modified polyurethane in this comparative example was kunlong HM2527.
Comparative example 2
The comparative example provides a UVLED curing coating, which comprises the following components in parts by weight:
the self-made modified polyurethane I is different from the polycaprolactone diol and the bisphenol A epoxy modified polyurethane in that the molecular weight of the polycaprolactone diol in the step S2 is 3000.
Comparative example 3
The comparative example provides a UVLED curing coating, which comprises the following components in parts by weight:
the self-made modified polyurethane II is distinguished from polycaprolactone diol and bisphenol A epoxy modified polyurethane in that the polycaprolactone diol in step S2 is replaced by a linear polyester diol (Wingda solid T1136, molecular weight 2000).
Comparative example 4
This comparative example provides a PMMA lamp shade having a thickness of 5 mm.
The coatings prepared in the above examples and comparative examples 1 to 3 were poured into a mold of 5mmx200mmx400mm and irradiated with a UVLED lamp having a wavelength of 395nm and an energy of 500mj/cm 2 The molded article was subjected to performance test.
The test method is as follows:
warp curvature: referring to SPC warp test standard, 30x20mm specification plate, baking at 80deg.C for 6H, measuring 4 angles with a feeler gauge;
curing time: the time required for curing the mixture to a depth of 5 mm;
scratch resistance: martindale test BSEN16094-2012;
butanone-resistant wiping: one kilogram of force is applied, and cotton cloth is dipped with butanone to wipe back and forth on the surface;
number of yellowing of the machine: energy 400mj/cm 2 。
The results of the performance test are shown in Table 1:
TABLE 1
The coating provided by each embodiment of the invention has high curing speed, can be deeply cured, and the warping degree and the yellowing performance of the molded product can be comparable to those of PMMA in comparative example 4, thus being applicable to advertising lampshades; meanwhile, compared with PMMA, the molded part of the embodiment of the invention has more excellent scratch resistance and solvent resistance.
As can be seen from the data in examples 1 to 4, the curing time of the coating gradually shortens with increasing polyurethane content in the system, and the solvent resistance and yellowing resistance of the molded article also increase.
From the data in examples 5 to 7, it is seen that the solvent resistance of the molded article increases as the amount of gaseous silicon in the system increases.
In comparative example 1, the coating was difficult to deeply cure and could not be deeply cured at a thickness of 5mm by using commercially available modified polyurethane as compared with example 7, and the scratch resistance, solvent resistance and yellowing resistance of the molded article were significantly lowered as compared with example 7.
Comparative example 2 provides a slightly increased cure time of the coating with a slightly reduced solvent resistance and yellowing resistance of the molded part compared to example 7, using a polycaprolactone diol having a greater molecular weight during the preparation of the homemade modified polyurethane I.
Comparative example 3 compared with example 7, the linear polyester diol is adopted to replace polycaprolactone diol in the preparation process of self-made modified polyurethane II, the curing time of the coating provided by the comparative example is obviously increased, the scratch resistance and the warping rate of the formed part are reduced, and the solvent resistance and the yellowing resistance are obviously reduced.
With the above-described preferred embodiments according to the present invention as an illustration, the above-described descriptions can be used by persons skilled in the relevant art to make various changes and modifications without departing from the scope of the technical idea of the present invention. The technical scope of the present invention is not limited to the description, but must be determined according to the scope of claims.
Claims (9)
1. The UVLED curing coating for molding the advertising lamp shade is characterized by comprising the following components in parts by weight:
50-80 parts of polycaprolactone diol and bisphenol A modified polyurethane;
0.1-0.3 part of polymerization inhibitor;
10-20 parts of active monomer;
0.5-1 part of antioxidant;
2-6 parts of gas silicon;
1-5 parts of dispersing agent;
0.1-0.5 part of defoaming agent;
0.1-0.5 part of leveling agent;
3-5 parts of an initiator;
the polycaprolactone diol and bisphenol A modified polyurethane is prepared according to the following method:
s1: mixing ethoxylated bisphenol A dimethacrylate, a catalyst 1173 and toluene, heating to 40-60 ℃, dropwise adding mercaptoethanol under the protection of inert gas, stirring and irradiating with an LED lamp with the wavelength of 365nm, monitoring the reaction by FTIR measurement, eliminating double bond absorption peak in the reactant, and removing the solvent to obtain a product A;
s2: mixing IPDI and DBTDL catalyst, dropwise adding a product A diluted by butyl acetate and polycaprolactone dihydric alcohol at 50 ℃, reacting, dropwise adding PET3A mixed with polymerization inhibitor BHT, heating to 60-80 ℃ until the content of-NCO groups is below 1%, sampling for infrared test, and monitoring characteristic absorption peaks at 2270cm of-NCO groups until the characteristic absorption peaks completely disappear, thus obtaining a PET3A end-capped product A;
s3: mixing mercaptomalonic acid, the PET3A end-capped product A, toluene and a catalyst 1173, heating to 40-60 ℃, under the protection of inert gas, stirring and irradiating with an LED lamp with the wavelength of 365nm, monitoring the reaction by FTIR measurement, eliminating double bond absorption peak in the reactant, and removing the solvent to obtain a product B;
s4: and mixing the product B, p-toluenesulfonic acid serving as a catalyst, hydroquinone and xylene, heating to 60-80 ℃, dropwise adding PET3A while stirring, monitoring the reaction through FTIR measurement, stopping dropwise adding PET3A after the absorption peak of carboxyl in the reactant disappears, and obtaining polycaprolactone diol and bisphenol A modified polyurethane after the reaction is finished.
2. The uv led curing coating for advertising lamp shade molding according to claim 1, wherein the mass ratio of the catalyst 1173 to the ethoxylated bisphenol a dimethacrylate in step S1 is 1: (1000-1010); the mass ratio of the mercaptoethanol to the ethoxylated bisphenol A dimethacrylate is (5-5.5): (25-26); the molar ratio of mercaptomalonic acid to PET3A end-capped product A in step S3 was 6:1, the volume of toluene was 4 times the sum of the volumes of mercaptomalonic acid and PET3A end-capped product A, and the mass of catalyst 1173 was 1% of the sum of the masses of mercaptomalonic acid and PET3A end-capped product A.
3. The uv led curing coating for advertising lamp shade molding of claim 1, wherein the polycaprolactone diol has a molecular weight of 2000.
4. A uv led curing coating for advertising lamp shade molding according to any one of claims 1-3, wherein the polymerization inhibitor is selected from at least one of quinone polymerization inhibitors, phenolic polymerization inhibitors.
5. A uv led curing coating for advertising lamp shade molding according to any one of claims 1-3, wherein the reactive monomer is selected from at least one of tripropylene glycol diacrylate, ethoxylated pentaerythritol tetraacrylate.
6. A uv led curing coating for advertising lamp shade molding according to any one of claims 1-3, wherein the antioxidant is selected from at least one of 1076, 330, 3114.
7. A uv led curing coating for advertising lamp shade molding according to any one of claims 1-3, wherein the dispersant is a macromolecular dispersant; the defoaming agent is an organosilicon defoaming agent or a polyether defoaming agent.
8. A uv led curing coating for advertising lamp shade molding according to any one of claims 1-3, wherein the leveling agent is an organosilicon leveling agent.
9. A uv led curing coating for advertising lamp shade molding according to any one of claims 1-3, wherein the initiator is selected from at least one of 1-hydroxycyclohexyl phenyl ketone, 2,4, 6-trimethylbenzoyl phosphorus phenoxide, 4-chlorobenzophenone.
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