CN103627282B - BOPP UV light-cured acrylate polymer coating and preparation method thereof - Google Patents
BOPP UV light-cured acrylate polymer coating and preparation method thereof Download PDFInfo
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- CN103627282B CN103627282B CN201310511523.8A CN201310511523A CN103627282B CN 103627282 B CN103627282 B CN 103627282B CN 201310511523 A CN201310511523 A CN 201310511523A CN 103627282 B CN103627282 B CN 103627282B
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- 239000011248 coating agent Substances 0.000 title claims abstract description 52
- 238000000576 coating method Methods 0.000 title claims abstract description 52
- 229920000058 polyacrylate Polymers 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- -1 acrylic ester Chemical class 0.000 claims abstract description 55
- 229920006378 biaxially oriented polypropylene Polymers 0.000 claims abstract description 51
- 239000011127 biaxially oriented polypropylene Substances 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 238000010792 warming Methods 0.000 claims description 21
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 14
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012965 benzophenone Substances 0.000 claims description 6
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 4
- 238000007711 solidification Methods 0.000 claims description 4
- 230000008023 solidification Effects 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 claims description 3
- TXFAWSBSQMMJSU-UHFFFAOYSA-N 5-(2-butylphenyl)nonan-5-amine Chemical compound CCCCC1=CC=CC=C1C(N)(CCCC)CCCC TXFAWSBSQMMJSU-UHFFFAOYSA-N 0.000 claims description 3
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- AJSHDAOMUKXVDC-UHFFFAOYSA-N butan-1-amine;sulfuric acid Chemical compound CCCC[NH3+].OS([O-])(=O)=O AJSHDAOMUKXVDC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 3
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 claims description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 2
- JUVLPJNXBKOSFH-UHFFFAOYSA-N 2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C1=CC(C(=O)C(N(C)C)CC)=CC=C1N1CCOCC1 JUVLPJNXBKOSFH-UHFFFAOYSA-N 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 2
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 abstract description 8
- 229920006222 acrylic ester polymer Polymers 0.000 abstract description 7
- 239000012752 auxiliary agent Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 6
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract description 2
- 230000008719 thickening Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000010008 shearing Methods 0.000 description 11
- 238000001723 curing Methods 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000000016 photochemical curing Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention belongs to acrylic ester polymer paint field, disclose a kind of BOPP UV light-cured acrylate polymer coating and its preparation method and application.This BOPP UV light-cured acrylate polymer coating comprises (methyl) acrylic ester prepolymer and light trigger, can be applicable in the coating of BOPP film.The present invention is by the kind of adjustment synthon, BOPP UV light-cured acrylate polymer coating can be obtained through reaction, this coating has good cohesive force and sticking power, a large amount of oxyethyl groups is there is in structure, make acrylic ester polymer coating have good snappiness and low-shrinkage, the degradation owing to using the auxiliary agent such as thickening material, tenderizer to cause can be avoided; There is curing reaction in the photoactivatable groups in structure, without the need to adding small molecules auxiliary agent, avoid that the high cohesive force that causes of small molecules shrinking percentage declines, the problem of easy to crack, easy generation line shape space and buckling deformation under uviolizing.
Description
Technical field
The invention belongs to acrylic ester polymer paint field, particularly a kind of BOPP UV light-cured acrylate polymer coating and its preparation method and application.
Background technology
Ultraviolet photocureable material at home and abroad comes into one's own with advantages such as its fast setting, low stain, less energy-consumption, high-level efficiency, is widely used in the aspects such as metal, timber, plastic coating, ink printing, textile printing, fibre coating, sizing agent.Pressure-sensitive sizing agent is called for short pressure sensitive adhesive, has easy to use, opens the rear feature generally not affecting adherend surface, is that a class uses sizing agent very widely.Pressure sensitive adhesive is normally base-material with long chain polymer, adds tackifying resin and tenderizer obtains; Sometimes force of cohesion and can be improved in order to improve liquidity and often add weighting agent, and add protective agent to improve stability and oxidation-resistance.Because long chain acrylate base polymer has good weathering resistance, thermotolerance, erosion resistance, oil-proofness, sticking power is high, and it on skin without impact, therefore it is widely used as pressure sensitive adhesive base-material, as Biaxially oriented polypropylene film (BOPP) (BOPP).But because acrylic ester polymer is generally chain linear structure, performance variation with temperature and larger change occurs, weathering resistance is poor, shrinking percentage is large, and increase the weighting agent normally small molecule monomer of force of cohesion, the volumetric shrinkage in solidification process is larger; If shrink the internal stress produced cannot discharge, the phenomenon of turning white after will causing occurring adhesive curing when using pressure sensitive adhesive, easily makes bonding material falls back.Pressure sensitive adhesive industry production adopts the mode such as thermofixation and hot melt often, big energy-consuming, and efficiency is lower.
Summary of the invention
In order to overcome the shortcoming of above-mentioned prior art with not enough, primary and foremost purpose of the present invention is to provide a kind of BOPP UV light-cured acrylate polymer coating.The present invention introduces oxyethyl group in acrylic ester prepolymer side chain, and acrylic ester prepolymer can be made to have, and shrinking percentage is low, snappiness is good, the excellent feature of dilution property; In the side chain of acrylic ester prepolymer, also introduce the reactive group that can carry out ultraviolet light polymerization simultaneously, make to contain unsaturated carbon-carbon double bond in the coating system obtained to carry out ultraviolet light polymerization, irradiation post-consumer polymer through UV-light occurs crosslinked, can when not adding small molecules auxiliary agent the force of cohesion of effective raising system, increase the service life.
Another object of the present invention is the preparation method providing a kind of above-mentioned BOPP UV light-cured acrylate polymer coating.
Still a further object of the present invention is to provide the application of above-mentioned BOPP UV light-cured acrylate polymer coating in the coating of BOPP film.
Object of the present invention is realized by following proposal:
A kind of BOPP UV light-cured acrylate polymer coating, comprises (methyl) acrylic ester prepolymer and light trigger; Described (methyl) acrylic ester prepolymer has following structure:
Wherein, R is H or CH
3, n=1 ~ 6, x=1 ~ 500, y=50 ~ 500, z=2 ~ 500.
Introduce in above-mentioned (methyl) acrylic ester prepolymer side chain and have oxyethyl group, have the advantages that shrinking percentage is low, snappiness is good, dilution property is excellent; Introduce the unsaturated double-bond reactive group that can carry out ultraviolet light polymerization simultaneously, the coating system obtained is made to carry out ultraviolet light polymerization, irradiation post-consumer polymer through UV-light occurs crosslinked, can when not adding small molecules auxiliary agent the force of cohesion of effective raising system, increase the service life.
Described light trigger refers to α, alpha, alpha-dimethyl oxygen base-α-phenyl acetophenone, α, α-diethoxy acetophenone, 2-hydroxyl-2 methyl isophthalic acids-phenyl-1-acetone, isopropyl phenyl-2-hydroxy-2-methyl acetone, 1-hydroxy-cyciohexyl benzophenone, 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone, 2-phenyl-2,2-dimethylamino-1-(4-morpholinyl phenyl)-1-butanone, 2, at least one in 4,6-trimethylbenzoyl diethyl phosphonate and benzophenone.
The mass ratio of described (methyl) acrylic ester prepolymer and light trigger is 100:(1 ~ 5).
A preparation method for above-mentioned BOPP UV light-cured acrylate polymer coating, comprises the following steps:
(methyl) glycidyl acrylate, ethoxyethoxyethyl acrylate, (methyl) alkyl acrylate, part initiator are added in solvent and mixes, reacting by heating, then add residue initiator and continue reaction; Add catalyzer, stopper, (methyl) vinylformic acid, temperature reaction, obtain (methyl) acrylic ester prepolymer, add light trigger, obtain BOPP UV light-cured acrylate polymer coating.
Solvent for use, (methyl) glycidyl acrylate, ethoxyethoxyethyl acrylate, (methyl) alkyl acrylate, initiator, catalyzer, stopper and (methyl) acrylic acid mass ratio are (150 ~ 200): (10 ~ 40): (50 ~ 80): (10 ~ 30): (3 ~ 4): (0.5 ~ 1): (0.2 ~ 0.5): (12 ~ 20).
The mass ratio of described (methyl) acrylic ester prepolymer and light trigger is 100:(1 ~ 5).
Described part initiator accounts for 60 ~ 75% of initiator total mass.
Described reacting by heating refers to stirring reaction 0.5 ~ 0.8h at 75 ~ 80 DEG C.
Preferably, described reacting by heating is carried out under the environment of logical nitrogen.
The described continuation reaction times is 10 ~ 15h.
Described temperature reaction refers to be warming up to 102 ~ 110 DEG C of reaction 4 ~ 5h.
Described solvent nail benzene, dimethylbenzene or pimelinketone.
Described (methyl) alkyl acrylate refers at least one in (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) butyl acrylate, isoamyl acrylate and (methyl) Ethyl acrylate.
Described initiator refers at least one in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), 2,2'-Azobis(2,4-dimethylvaleronitrile) and azo dicyclohexyl formonitrile HCN.
Described catalyzer refers at least one in Tetrabutyl amonium bromide, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate, benzyl triethyl ammonium bromide, bromination tributyl benzylamine, trioctylphosphine brometo de amonio, tri-n-octyl methyl ammonium chloride and 4-butyl ammonium fluoroborate.
Described stopper refers at least one in Resorcinol, para benzoquinone, toluhydroquinone, MEHQ, 2-Tert. Butyl Hydroquinone and 2,5 di tert butyl hydroquinone.
The application of above-mentioned BOPP UV light-cured acrylate polymer coating in the coating of BOPP film, realized by following methods: use coating roller to be evenly coated on BOPP film by BOPP UV light-cured acrylate polymer coating, under being placed in ultraviolet lamp, irradiate solidification.
The wavelength region of described ultraviolet lamp is 200 ~ 400nm.
Preferably, the thickness of described coating is 0.08mm.
Mechanism of the present invention is:
The present invention introduces oxyethyl group in acrylic ester prepolymer side chain, and acrylic ester prepolymer can be made to have, and shrinking percentage is low, snappiness is good, the excellent feature of dilution property; In the side chain of acrylic ester prepolymer, also introduce the reactive group that can carry out ultraviolet light polymerization simultaneously, make to contain unsaturated carbon-carbon double bond in the system obtained to carry out ultraviolet light polymerization, irradiation post-consumer polymer through UV-light occurs crosslinked, can when not adding small molecules auxiliary agent the force of cohesion of effective raising system, increase the service life.
The present invention, relative to prior art, has following advantage and beneficial effect:
(1) the present invention is by the kind of adjustment synthon, can obtain a series of BOPP UV light-cured acrylate polymer coating through reaction.
(2) UV light-cured acrylate polymer coating of the present invention has good cohesive force and sticking power, a large amount of oxyethyl groups is there is in structure, make acrylic ester polymer coating have good snappiness and low-shrinkage, the degradation owing to using the auxiliary agent such as thickening material, tenderizer to cause can be avoided; Meanwhile, there is curing reaction in photoactivatable groups appropriate in structure under uviolizing, and make the solidification of polymkeric substance appropriateness, the small molecules auxiliary agent that need not add increases force of cohesion can improve the force of cohesion of polymkeric substance.Can effectively avoid the high cohesive force that causes of small molecules shrinking percentage to decline, easily cracking, easily produce the problem of line shape space and buckling deformation.
(3) UV light-cured acrylate polymer coating of the present invention takes the mode of ultraviolet light polymerization to solidify, and process is simple rapidly, pollution is few, effectively can improve production rate, energy-conserving and environment-protective.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of the acrylic ester prepolymer S1 that embodiment 1 prepares.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
In the following example, each performance perameter is according to following standard test:
The volumetric shrinkage of polymkeric substance: measure by ISO3521;
The shearing resistance of polymkeric substance: measure by GB/T7124;
The annular initial adhesive strength of polymkeric substance: measure by FINATFTM9-2003;
180 ° of stripping strengths of polymkeric substance: measure by GB/2792-1998;
Polymkeric substance hold viscosity: measure by GB/4851-1998.
The embodiment 1:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the toluene getting 150 parts is placed in the reactor with agitator, prolong, and add glycidyl acrylate 40 parts, ethoxyethoxyethyl acrylate 50 parts, methyl acrylate 10 parts, Diisopropyl azodicarboxylate 2 parts successively, be uniformly mixed in the environment of logical nitrogen, be warming up to 75 DEG C, reaction 0.5h, add Diisopropyl azodicarboxylate 1 part again, continue reaction 10h, add the Tetrabutyl amonium bromide of 0.5 part, the hydroquinone of polymerization retarder of 0.2 part, 12 parts, vinylformic acid, be warming up to 102 DEG C of reaction 4h, obtained acrylic ester prepolymer S1;
Fig. 1 is the infrared spectrogram of the acrylic ester prepolymer S1 that step (1) obtains, as can be seen from FIG., at 1621cm
-1having there is double bond absorption peak in place, shows that acrylic acid double bond is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group.
(2) 1 part of α can be added in the acrylic ester prepolymer S1 of UV photocuring at gained, alpha, alpha-dimethyl oxygen base-α-phenyl acetophenone, mixes, and is coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.62%, shearing resistance 4.55 × 10
5pa, annular initial bonding strength 8.38N/25mm, 180 ° of stripping strengths are 8.09N/25mm, hold sticky 3.12h.
The embodiment 2:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the pimelinketone getting 200 parts is placed in agitator, in the reactor of prolong, and add glycidyl acrylate 10 parts successively, ethoxyethoxyethyl acrylate 80 parts, ethyl propenoate 10 parts, initiator 2,2'-Azobis(2,4-dimethylvaleronitrile) 3 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 80 DEG C, reaction 0.6h, add 2,2'-Azobis(2,4-dimethylvaleronitrile) 1 part again, after continuing reaction 15h, add the α of 1 part, α-diethoxy acetophenone, the para benzoquinone of 0.5 part, 20 parts, vinylformic acid, be warming up to 110 DEG C of reaction 5h, obtained acrylic ester prepolymer S2.Infrared test is done to S2, from result, at 1621cm
-1having there is double bond absorption peak in place, shows that acrylic acid double bond is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group;
(2) 5 parts of α can be added in the acrylic ester prepolymer S2 of UV photocuring at gained, α-diethoxy acetophenone, mixes, and is coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 200nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.65%, shearing resistance 3.63 × 10
5pa, annular initial bonding strength 8.28N/25mm, 180 ° of stripping strengths are 8.11N/25mm, hold sticky 3.09h.
The embodiment 3:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the dimethylbenzene getting 180 parts is placed in agitator, in the reactor of prolong, and add glycidyl acrylate 20 parts successively, ethoxyethoxyethyl acrylate 50 parts, propyl acrylate 30 parts, 2,2'-Azobis(2,4-dimethylvaleronitrile) 2.5 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 78 DEG C, reaction 0.7h, add 2,2'-Azobis(2,4-dimethylvaleronitrile) 1 part again, after continuing reaction 12h, add the 4-butyl ammonium hydrogen sulfate of 0.6 part, the toluhydroquinone of 0.3 part, 15 parts, vinylformic acid, be warming up to 105 DEG C of reaction 4.5h, obtained acrylic ester prepolymer S3.Infrared test is done to S3, from result, at 1621cm
-1having there is double bond absorption peak in place, shows that acrylic acid double bond is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group;
(2) 4 parts of 2-hydroxyl-2 methyl isophthalic acids-phenyl-1-acetone can be added in the acrylic ester prepolymer S3 of UV photocuring at gained, mix, and be coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.66%, shearing resistance 3.62 × 10
5pa, annular initial bonding strength 8.35N/25mm, 180 ° of stripping strengths are 8.06N/25mm, hold sticky 3.05h.
The embodiment 4:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the pimelinketone getting 170 parts is placed in agitator, in the reactor of prolong, and add glycidyl acrylate 20 parts successively, ethoxyethoxyethyl acrylate 60 parts, butyl acrylate 20 parts, azo dicyclohexyl formonitrile HCN 2.5 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 78 DEG C, reaction 0.8h, add azo dicyclohexyl formonitrile HCN 1 part again, after continuing reaction 13h, add the benzyl triethyl ammonium bromide of 0.8 part, the MEHQ of 0.4 part, 16 parts, vinylformic acid, be warming up to 105 DEG C of reaction 4h, obtained acrylic ester prepolymer S4. does infrared test to S4, from result, at 1621cm
-1having there is double bond absorption peak in place, shows that acrylic acid double bond is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group,
(2) 3 parts of isopropyl phenyl-2-hydroxy-2-methyl acetone can be added in the acrylic ester prepolymer S4 of UV photocuring at gained, mix, and be coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 400nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.70%, shearing resistance 3.66 × 10
5pa, annular initial bonding strength 8.34N/25mm, 180 ° of stripping strengths are 8.13N/25mm, hold sticky 3.10h.
The embodiment 5:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the toluene getting 150 parts is placed in agitator, in the reactor of prolong, and add glycidyl methacrylate 40 parts successively, ethoxyethoxyethyl acrylate 50 parts, methyl methacrylate 10 parts, Diisopropyl azodicarboxylate 2 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 75 DEG C, reaction 0.5h, add Diisopropyl azodicarboxylate 1 part again, after continuing reaction 10h, add the bromination tributyl benzylamine of 0.5 part, the 2-Tert. Butyl Hydroquinone of 0.2 part, methacrylic acid 12 parts, be warming up to 106 DEG C of reaction 5h, obtained acrylic ester prepolymer S5.Infrared test is done to S5, from result, at 1621cm
-1having there is double bond absorption peak in place, shows that the double bond of methacrylic acid is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group;
(2) 1 part of 1-hydroxy-cyciohexyl benzophenone can be added in the methacrylate prepolymers S5 of UV photocuring at gained, mix, and be coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.71%, shearing resistance 3.68 × 10
5pa, annular initial bonding strength 8.25N/25mm, 180 ° of stripping strengths are 8.04N/25mm, hold sticky 3.06h.
The embodiment 6:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the pimelinketone getting 200 parts is placed in agitator, in the reactor of prolong, and add glycidyl methacrylate 10 parts successively, ethoxyethoxyethyl acrylate 80 parts, β-dimethyl-aminoethylmethacrylate 10 parts, initiator 3 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 80 DEG C, reaction 0.5h, add 2,2'-Azobis(2,4-dimethylvaleronitrile) 1 part again, after continuing reaction 15h, add the trioctylphosphine brometo de amonio of 1 part, 0.5 part 2, 5-di-tert-butyl hydroquinone, methacrylic acid 20 parts, be warming up to 108 DEG C of reaction 5h, obtained acrylic ester prepolymer S6.Infrared test is done to S6, from result, at 1621cm
-1having there is double bond absorption peak in place, shows that the double bond of methacrylic acid is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group;
(2) 5 parts of 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone can be added in the methacrylate prepolymers S6 of UV photocuring at gained, mix, and be coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.75%, shearing resistance 3.67 × 10
5pa, annular initial bonding strength 8.29N/25mm, 180 ° of stripping strengths are 7.98N/25mm, hold sticky 3.13h.
The embodiment 7:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the dimethylbenzene getting 180 parts is placed in agitator, in the reactor of prolong, and add glycidyl methacrylate 20 parts successively, ethoxyethoxyethyl acrylate 50 parts, butyl methacrylate 30 parts, 2,2'-Azobis(2,4-dimethylvaleronitrile) 2.5 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 78 DEG C, reaction 0.5h, add 2,2'-Azobis(2,4-dimethylvaleronitrile) 1 part again, after continuing reaction 12h, add the 4-butyl ammonium fluoroborate of 0.6 part, the Resorcinol of 0.3 part, methacrylic acid 15 parts, be warming up to 103 DEG C of reaction 4.5h, obtained acrylic ester prepolymer S7.Infrared test is done to S7, from result, at 1621cm
-1having there is double bond absorption peak in place, shows that the double bond of methacrylic acid is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group;
(2) 4 parts of 2-phenyl-2 can be added in the methacrylate prepolymers S7 of UV photocuring at gained, 2-dimethylamino-1-(4-morpholinyl phenyl)-1-butanone, mix, and be coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.70%, shearing resistance 3.69 × 10
5pa, annular initial bonding strength 8.31N/25mm, 180 ° of stripping strengths are 7.97N/25mm, hold sticky 3.11h.
The embodiment 8:BOPP preparation of UV light-cured acrylate polymer coating
(1) by weight, the pimelinketone getting 170 parts is placed in agitator, in the reactor of prolong, and add glycidyl methacrylate 20 parts successively, ethoxyethoxyethyl acrylate 60 parts, N-Hexyl methacrylate 20 parts, azo dicyclohexyl formonitrile HCN 2.5 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 78 DEG C, reaction 0.5h, add azo dicyclohexyl formonitrile HCN 1 part again, after continuing reaction 13h, add the tri-n-octyl methyl ammonium chloride of 0.8 part, the 2-Tert. Butyl Hydroquinone of 0.4 part, methacrylic acid 16 parts, be warming up to 104 DEG C of reaction 4h, obtained acrylic ester prepolymer S8.Infrared test is done to S8, from result, at 1621cm
-1having there is double bond absorption peak in place, shows that the double bond of methacrylic acid is successfully linked in binary polymerization objects system, thus introduce ultraviolet curing group;
(2) 3 part of 2,4,6-trimethylbenzoyl diethyl phosphonate can be added in the methacrylate prepolymers S8 of UV photocuring at gained, mix, and be coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.72%, shearing resistance 3.64 × 10
5pa, annular initial bonding strength 8.28N/25mm, 180 ° of stripping strengths are 8.03N/25mm, hold sticky 3.10h.
Comparative example 1: not containing the preparation of the acrylic ester polymer of optical active group
(1) by weight, the pimelinketone getting 170 parts is placed in the reactor with agitator, prolong, and add glycidyl acrylate 20 parts, ethoxyethoxyethyl acrylate 60 parts, butyl acrylate 20 parts, azo dicyclohexyl formonitrile HCN 2.5 parts successively, be uniformly mixed in the environment of logical nitrogen, be warming up to 78 DEG C, reaction 0.5h, then add azo dicyclohexyl formonitrile HCN 1 part, after continuing reaction 13h, obtained not containing the acrylic ester prepolymer T1 of optical active group;
(2) be not coated with the thick film of 0.08mm containing the acrylic ester prepolymer T1 of optical active group at BOPP film surface by gained, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 1.63%, shearing resistance 2.06 × 10
5pa, annular initial bonding strength 8.25N/25mm, 180 ° of stripping strengths are 8.21N/25mm, hold sticky 1.84h.
Comparative example 2: not containing the preparation of the acrylic ester polymer of ethoxy side chain
(1) by weight, the pimelinketone getting 170 parts is placed in agitator, in the reactor of prolong, and add glycidyl acrylate 20 parts successively, methyl acrylate 60 parts, butyl acrylate 20 parts, azo dicyclohexyl formonitrile HCN 2.5 parts, be uniformly mixed in the environment of logical nitrogen, be warming up to 78 DEG C, reaction 0.5h, add azo dicyclohexyl formonitrile HCN 1 part again, after continuing reaction 13h, add the tri-n-octyl methyl ammonium chloride of 0.8 part, the 2-Tert. Butyl Hydroquinone of 0.4 part, 16 parts, vinylformic acid, being warming up to 105 DEG C of reaction 4h obtains not containing the acrylic ester prepolymer T2 of ethoxy side chain,
(2) gained not containing the acrylic ester prepolymer T2 of ethoxy side chain in add 3 parts of benzophenone, mix, and be coated with the thick film of 0.08mm at BOPP film surface, distance wavelength is the ultraviolet lamp 4cm of 365nm, and it is as follows to irradiate performance after 10 seconds:
Volumetric shrinkage 5.37%, shearing resistance 1.94 × 10
5pa, annular initial bonding strength 7.98N/25mm, 180 ° of stripping strengths are 7.88N/25mm, hold sticky 2.67h.
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from spirit of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (10)
1. a BOPP UV light-cured acrylate polymer coating, is characterized in that comprising (methyl) acrylic ester prepolymer and light trigger; Described (methyl) acrylic ester prepolymer has following structure:
Wherein, R is H or CH
3, n=1 ~ 6, x=1 ~ 500, y=50 ~ 500, z=2 ~ 500.
2. BOPP UV light-cured acrylate polymer coating according to claim 1, it is characterized in that: described light trigger refers to α, alpha, alpha-dimethyl oxygen base-α-phenyl acetophenone, α, α-diethoxy acetophenone, 2-hydroxyl-2 methyl isophthalic acids-phenyl-1-acetone, isopropyl phenyl-2-hydroxy-2-methyl acetone, 1-hydroxy-cyciohexyl benzophenone, 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone, 2-phenyl-2, 2-dimethylamino-1-(4-morpholinyl phenyl)-1-butanone, 2, 4, at least one in 6-trimethylbenzoyl diethyl phosphonate and benzophenone.
3. BOPP UV light-cured acrylate polymer coating according to claim 1, is characterized in that: the mass ratio of described (methyl) acrylic ester prepolymer and light trigger is 100:(1 ~ 5).
4. the preparation method for UV light-cured acrylate polymer coating of the BOPP according to any one of claims 1 to 3, is characterized in that comprising the following steps:
(methyl) glycidyl acrylate, ethoxyethoxyethyl acrylate, (methyl) alkyl acrylate, part initiator are added in solvent and mixes, reacting by heating, then add residue initiator and continue reaction; Add catalyzer, stopper, (methyl) vinylformic acid, temperature reaction, obtain (methyl) acrylic ester prepolymer, add light trigger, obtain BOPP UV light-cured acrylate polymer coating.
5. the preparation method of BOPP UV light-cured acrylate polymer coating according to claim 4, is characterized in that: solvent for use, (methyl) glycidyl acrylate, ethoxyethoxyethyl acrylate, (methyl) alkyl acrylate, initiator, catalyzer, stopper and (methyl) acrylic acid mass ratio are (150 ~ 200): (10 ~ 40): (50 ~ 80): (10 ~ 30): (3 ~ 4): (0.5 ~ 1): (0.2 ~ 0.5): (12 ~ 20).
6. the preparation method of BOPP UV light-cured acrylate polymer coating according to claim 4, is characterized in that: the mass ratio of described (methyl) acrylic ester prepolymer and light trigger is 100:(1 ~ 5).
7. the preparation method of BOPP UV light-cured acrylate polymer coating according to claim 4, is characterized in that: described part initiator accounts for 60 ~ 75% of initiator total mass; Described reacting by heating refers to stirring reaction 0.5 ~ 0.8h at 75 ~ 80 DEG C; The described continuation reaction times is 10 ~ 15h; Described temperature reaction refers to be warming up to 102 ~ 110 DEG C of reaction 4 ~ 5h.
8. the preparation method of BOPP UV light-cured acrylate polymer coating according to claim 4, is characterized in that: described solvent nail benzene, dimethylbenzene or pimelinketone; Described (methyl) alkyl acrylate refers at least one in (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) butyl acrylate, isoamyl acrylate and (methyl) Ethyl acrylate; Described initiator refers at least one in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), 2,2'-Azobis(2,4-dimethylvaleronitrile) and azo dicyclohexyl formonitrile HCN; Described catalyzer refers at least one in Tetrabutyl amonium bromide, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate, benzyl triethyl ammonium bromide, bromination tributyl benzylamine, trioctylphosphine brometo de amonio, tri-n-octyl methyl ammonium chloride and 4-butyl ammonium fluoroborate; Described stopper refers at least one in Resorcinol, para benzoquinone, toluhydroquinone, MEHQ, 2-Tert. Butyl Hydroquinone and 2,5 di tert butyl hydroquinone.
9. the application of UV light-cured acrylate polymer coating in the coating of BOPP film of the BOPP according to any one of claims 1 to 3, it is characterized in that being realized by following methods: use coating roller to be evenly coated on BOPP film by BOPP UV light-cured acrylate polymer coating, under being placed in ultraviolet lamp, irradiate solidification.
10. the application of BOPP UV light-cured acrylate polymer coating according to claim 9 in the coating of BOPP film, is characterized in that: the wavelength region of described ultraviolet lamp is 200 ~ 400nm; The thickness of described coating is 0.08mm.
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| CN1718567A (en) * | 2004-07-05 | 2006-01-11 | 北京清华紫光英力化工技术有限责任公司 | Acrylate kind oligomer with side chain containing unsaturated functional group, its proparation method and light solidifying paint composition containing same |
| CN103059316A (en) * | 2012-12-31 | 2013-04-24 | 中科院广州化学有限公司 | Polyurethane/polyacrylate copolymer modified by organic fluoride and ultraviolet curing coating prepared by polyurethane/polyacrylate copolymer |
| CN103059315A (en) * | 2012-12-31 | 2013-04-24 | 中科院广州化学有限公司 | Polyurethane/polyacrylate copolymer and BOPP (Biaxially-oriented Polypropylene) film prepared by same |
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| CN1718567A (en) * | 2004-07-05 | 2006-01-11 | 北京清华紫光英力化工技术有限责任公司 | Acrylate kind oligomer with side chain containing unsaturated functional group, its proparation method and light solidifying paint composition containing same |
| CN103059316A (en) * | 2012-12-31 | 2013-04-24 | 中科院广州化学有限公司 | Polyurethane/polyacrylate copolymer modified by organic fluoride and ultraviolet curing coating prepared by polyurethane/polyacrylate copolymer |
| CN103059315A (en) * | 2012-12-31 | 2013-04-24 | 中科院广州化学有限公司 | Polyurethane/polyacrylate copolymer and BOPP (Biaxially-oriented Polypropylene) film prepared by same |
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