CN109762397A - A kind of UV Photocurable composition containing amino ketone photoinitiator - Google Patents
A kind of UV Photocurable composition containing amino ketone photoinitiator Download PDFInfo
- Publication number
- CN109762397A CN109762397A CN201910052026.3A CN201910052026A CN109762397A CN 109762397 A CN109762397 A CN 109762397A CN 201910052026 A CN201910052026 A CN 201910052026A CN 109762397 A CN109762397 A CN 109762397A
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- China
- Prior art keywords
- acrylate
- photocurable composition
- diacrylate
- phenyl
- methyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 47
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 230000000694 effects Effects 0.000 claims abstract description 10
- 238000000576 coating method Methods 0.000 claims abstract description 8
- 239000011248 coating agent Substances 0.000 claims abstract description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 5
- 238000003847 radiation curing Methods 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 239000011734 sodium Substances 0.000 claims abstract description 5
- 238000003848 UV Light-Curing Methods 0.000 claims abstract description 4
- 238000000016 photochemical curing Methods 0.000 claims abstract description 4
- -1 acridine compound Chemical class 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 239000000049 pigment Substances 0.000 claims description 11
- 239000004925 Acrylic resin Substances 0.000 claims description 9
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- LJRSZGKUUZPHEB-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COC(C)COC(=O)C=C LJRSZGKUUZPHEB-UHFFFAOYSA-N 0.000 claims description 4
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 4
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002518 antifoaming agent Substances 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 4
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000006188 2-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 claims description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 2
- IQQVCMQJDJSRFU-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO IQQVCMQJDJSRFU-UHFFFAOYSA-N 0.000 claims description 2
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- GBNLYMPUUMKHTO-UHFFFAOYSA-N C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C)OC(CC(CO)(CO)CO)(OCC)OCC Chemical compound C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C)OC(CC(CO)(CO)CO)(OCC)OCC GBNLYMPUUMKHTO-UHFFFAOYSA-N 0.000 claims description 2
- XBOGYLXKVSMMFY-UHFFFAOYSA-N C(C)OP(=O)C(C1=C(C(=C(C=C1)C)C)C)=O Chemical class C(C)OP(=O)C(C1=C(C(=C(C=C1)C)C)C)=O XBOGYLXKVSMMFY-UHFFFAOYSA-N 0.000 claims description 2
- XAHHPYJTLUQPKK-UHFFFAOYSA-N C(C=C)(=O)O.C(C=C)(=O)O.C(C)O.C(C)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.C(C)O.C(C)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O XAHHPYJTLUQPKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
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- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 claims description 2
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 claims description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical class CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 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
- 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 description 2
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- 239000006229 carbon black Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
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- 229920001577 copolymer Polymers 0.000 claims description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 2
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 claims description 2
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- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 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
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
Abstract
A kind of UV Photocurable composition containing amino ketone photoinitiator, the composition are suitable for photocuring system, are primarily adapted for use in UV curing system, are particularly suitable for UV curable ink and coating system；The UV Photocurable composition activity containing amino ketone photoinitiator is high, both can also pass through UV-LED radiation curing by high-pressure sodium lamp radiation curing；Both the surface layer solidification that coating may be implemented, also may be implemented deep cure；It is with a wide range of applications.
Description
Technical field
The present invention relates to a kind of UV Photocurable composition containing amino ketone photoinitiator, the composition are suitable for photocuring body
System, is primarily adapted for use in UV curing system, is particularly suitable for UV curable ink and coating system.
Background technique
Amino ketone compound is a kind of efficient free radical (I) type photoinitiator, and effective absorption peak is 300-
400nm produces free radical polymerization after illumination, and laser curing velocity is fast, is suitable for thick film deep cure.It is particularly suitable for
The rapid curing of pigmented system.
Presently commercially available amino ketones mainly has 2 kinds, is 2- phenyl benzyl -2- dimethyl amine -1- (4- morpholine benzyl phenyl) respectively
Butanone (UV369), 2- methyl-1-(4- methyl mercapto phenyl)-2- morpholinyl-1- acetone (Irgacure907)；There are two by UV369
It is a clearly disadvantageous, one is dissolubility is poor in all kinds of unsaturated performed polymers and monomer, prepare difficult, the low-temperature stabilization of formula
Property is poor, is easy to be precipitated from formula when especially additive amount is more than 5%；The second is UV369 is causing unsaturated component polymerization
When along with more serious xanthochromia is generated, cannot be used in fields such as food packaging, varnish paint, white inks；And
Irgacure907 can be decomposed in Light Curing generates sulfidomethyl benzaldehyde, irritant smell and certain toxicity, by
European Union's limitation uses.
For disadvantages described above, in recent years, also there are relevant report, Chinese patent for the research for the two substitute
CN101724099, which discloses ([1,1- xenyl] -4- base) -2- methyl -2- morpholinopropane -1- ketone, can substitute Irgacure
907,.The compound is free of element sulphur, applied to embodying excellent yellowing resistance, light in UV radical photopolymerization curing system
According to bad smell will not be generated after decomposition.But find in practical applications, the photoinitiator dissolubility is poor, Yi Shenghua, meeting
Production equipment and light source are polluted, are not a perfect substitutes.
Chinese patent CN201711472418 discloses a series of fluorenyl aminoketone compounds, such compound is causing
Although not generating apparent Yellowing in Light Curing, toxicity itself is also very low, and fluorenyl aromatic structure determines molecule
Inactive portion accounting is too big in structure, and initiation activity needs to improve additive amount not as good as Irgacure 907 and can be only achieved same effect
The raising of fruit, additive amount significantly increases cost.So it is not still a kind of good substitute.
Develop the UV light that can effectively solve the above problems and have advantage competition power in economy and environment friendly
Solidification composition filling is still one of the important topic that the current industrial field faces.
Summary of the invention
The present invention is intended to provide a kind of UV Photocurable composition of photoinitiator containing aminoketones, to solve Irgacure
907 lead to the problem of peculiar smell and toxicity in Light Curing.
A kind of UV Photocurable composition containing amino ketone photoinitiator, by each at being grouped as of following parts by weight:
In the UV Photocurable composition containing amino ketone photoinitiator, photoinitiator can be individually as shown in formula (I)
The compound of structure is also possible to the mixture of formula (I) compound and other photoinitiators.
In the UV Photocurable composition containing amino ketone photoinitiator, photoinitiator is selected from 2- hydroxy-methyl phenyl third
Alkane -1- ketone, 1- hydroxyl-cyclohexyl-phenyl ketone, (2,4,6- trimethyl-benzoyl) diphenyl phosphine oxide, bis- (2,4,6-
Trimethylbenzoyl)-phenyl phosphine oxide, 2,4,6 1 trimethylbenzoyl phosphinic acid ethyl esters, 2- phenyl benzyl -2- dimethyl amine -
1- (4- morpholine benzyl phenyl) butanone, benzophenone, 4- phenyl benzophenone, 4- methyl benzophenone, isopropyl thioxanthone, 2,
One or more of 4- diethyl thioxanthone, methyl o-benzoylbenzoate, methyl o-benzoylbenzoate.
In the UV Photocurable composition containing amino ketone photoinitiator, alkenes unsaturated group prepolymer includes epoxy third
Olefin(e) acid resin, polyurethane acrylic resin, polyester acrylate resin, polyoxyalkylene acrylate resin, pure acrylate resin, vinyl
Resin or their any mixture.
In the UV Photocurable composition containing amino ketone photoinitiator, alkenes unsaturated group monomer classification includes propylene
Acid alkyl ester, methacrylic acid hydroxy ester, (methyl) acrylate with cyclic structure or phenyl ring, the dilution of vinyl activity
Agent, glycols diacrylate, propandiols diacrylate, other glycols diacrylates, polyfunctional group activity are dilute
Release agent, alkoxylated acrylate, acrylic acid two dislike luxuriant ester, alkoxylated bis-phenol A bis- (methyl) acrylate, vinyl ethers
Reactive diluent, (methyl) acrylate of the end group containing methoxy, phosphorous flame retardant acrylate；
In the UV Photocurable composition containing amino ketone photoinitiator, alkenes unsaturated group monomer refers specifically to acrylic acid
Different monooctyl ester (2-EHA), isodecyl acrylate (IDA), lauryl acrylate (LA), glycidyl methacrylate (GMA), first
Base isobornyl acrylate (IBOA), phenoxyethyl acrylate (POEA), 1,4-butanediol diacrylate (BDDA), 1,6-
Hexanediyl ester (HDDA), phthalic acid diethanol diacrylate (PDDA), diethylene glycol diacrylate
(DEGDA), triethylene glycol diacrylate (TEGDA), pentaerythritol triacrylate (PETA), pentaerythritol tetraacrylate
(PETTA), two contracting trimethylolpropane tetra-acrylate (DTNPTA) polyethyleneglycol diacrylates (PEGDA), neopentyl glycol
Diacrylate (NPGDA), two contracting propylene glycol double methacrylates (DPGDA), double pentaerythritol methacrylate (DPHA) double seasons
Penta tetrol, five acrylate (DPPA), triethoxy trimethylolpropane trimethacrylate (3EOTMPTA), trihydroxy methyl third
Alkane triacrylate (TMPTA), tri (propylene glycol) diacrylate (TPGDA).
In the UV Photocurable composition containing amino ketone photoinitiator, other auxiliary agents include filler, pigment, levelling agent,
Dispersing agent, defoaming agent, polymerization inhibitor or their any mixture.
Filler includes talcum powder, silica, calcene, barium sulfate and kaolin；
Pigment includes white pigment, black pigment, color pigment；It specifically can be titanium dioxide, carbon black, phthalocyanine blue, pigment
Red, pigment yellow, phthalocyanine green, forever solid orange, solid palm fibre and phthalocyanine are purple forever；
Levelling agent includes polyacrylate, modified cellulose, organic silicone grease and fluorocarbon resin；
Dispersing agent includes that high molecular polymer, electroneutral polyamide and polyester mixture, low molecular weight unsaturated carboxylic acid are poly-
Close object, the copolymer containing acidic-group, the alkyl ammonium salt of the block copolymer containing acidic-group, urethane derivative and poly- third
Olefin(e) acid ester；
Defoaming agent includes organic silicon modified by polyether, higher alcohols, dimethyl silicone polymer；
Polymerization inhibitor includes quinhydrones, Hydroquinone monomethylether, hydroquinone, p-hydroxyanisole.
UV Photocurable composition provided by the invention containing amino ketone photoinitiator is suitable for photocuring system, main to be applicable in
In UV curing system, it is particularly suitable for UV curable ink and coating system；The composition is after body surface film
It is formed through ultraviolet source radiation curing, ultraviolet source used can be high-pressure sodium lamp light source, be also possible to UV-LED light source；It is ultraviolet
Optical source wavelength range can be 200nm-500nm.
The present invention has the advantage that
(1) the UV Photocurable composition provided by the invention containing amino ketone photoinitiator is in ultraviolet-curing paint or oil
Cause that activity is high, and curing time is short in ink, solidification process also few VOC emissions, are a kind of environmentally protective ultraviolet light solidifications
Formula.
(2) the UV Photocurable composition provided by the invention containing amino ketone photoinitiator can both pass through high-pressure sodium lamp spoke
Solidification is penetrated, can also be by UV-LED radiation curing, it can great energy saving when being solidified using LED radiation.
(3) deep layer of coating had both may be implemented in the UV Photocurable composition provided by the invention containing amino ketone photoinitiator
Surface layer solidification also may be implemented, to keep curing of coatings more thorough in solidification.
Specific embodiment
The present invention will be described further by following embodiments.
The UV Photocurable composition containing amino ketone photoinitiator that following embodiment provides is printed applied to ultraviolet cured adhesive
The specific formula of ink is shown in Table 1:
Table 1
Composition prepared by the present embodiment is coated on sheet glass, 365nmUV-LED lamp radiation under solidify 10s,
30s, 60s, 120s judge the surface drying of cured film to characterize curing rate with finger-press method.
Adhesive force measurement: cured film adhesive force is measured using frame method.
Determination of Hardness: pencil hardness method test solidification film hardness is utilized.
Test result is as follows for embodiment 1-3 and comparative example (chooses photoinitiator Irgacure 907+ITX to compare
):
| Embodiment | Curing rate | Adhesive force | Hardness | Smell |
| Embodiment 1 | 60s | 4 | 2B | 1 |
| Embodiment 2 | 60s | 4 | 2B | 1 |
| Embodiment 3 | 120s | 4 | HB | 1 |
| Comparative example 4 | 120s | 4 | HB | 3 |
It can be seen from the data in the table that the UV Photocurable composition of present invention initiator containing amino ketones is in UV- under the same terms
Cause activity compared with comparative example quite under LED light radiation, but there is smaller smell；Individually make in different colours ink system
Effect is also fine when with formula (1) compound as initiator.
The UV Photocurable composition containing amino ketone photoinitiator that following embodiment provides is applied to ultraviolet-curing paint
Specific formula be shown in Table 2: table 2
Composition prepared by the present embodiment is coated on sheet glass, is solidified under the radiation of 2000w high-pressure sodium lamp lamp
10s, 20s, 40s, 80s, 120s judge the surface drying of cured film to characterize curing rate with finger-press method.
Adhesive force measurement: cured film adhesive force is measured using frame method.
Determination of Hardness: pencil hardness method test solidification film hardness is utilized.
Xanthochromia test: according to GB/T1865-2009 standard determination.
Test result is as follows (choose photoinitiator Irgacure 907 and do comparative run):
| Embodiment | Curing rate | Adhesive force | Hardness | Xanthochromia (△ E) | Smell |
| Embodiment 5 | 40s | 4 | HB | 0.22 | 1 |
| Embodiment 6 | 40s | 4 | HB | 0.21 | 1 |
| Embodiment 7 | 40s | 4 | HB | 0.25 | 1 |
| Comparative example 8 | 40s | 5 | HB | 0.32 | 3 |
It can be seen from the data in the table that the UV Photocurable composition of present invention initiator containing amino ketones is in high pressure under the same terms
There is smaller smell and xanthochromia compared with comparative example under mercury lamp radiation；It can be widely suitable for photocureable coating industry.
Claims (10)
1. a kind of UV Photocurable composition containing amino ketone photoinitiator, which is characterized in that by each at grouping of following parts by weight
At:
2. UV Photocurable composition according to claim 1, which is characterized in that the amino ketone photoinitiator can be individually
The compound of the structure as shown in formula (I), is also possible to the mixture of formula (I) compound and other photoinitiators.
3. UV Photocurable composition according to claim 2, which is characterized in that other photoinitiators are selected from 2- hydroxyl-
Aminomethyl phenyl propane -1- ketone, 1- hydroxyl-cyclohexyl-phenyl ketone, (2,4,6- trimethyl-benzoyl) diphenyl phosphine oxide,
Bis- (2,4,6- trimethylbenzoyl)-phenyl phosphine oxides, 2,4,6 1 trimethylbenzoyl phosphinic acid ethyl esters, 2- phenyl benzyl -2-
Dimethyl amine -1- (4- morpholine benzyl phenyl) butanone, benzophenone, 4- phenyl benzophenone, 4- methyl benzophenone, isopropyl sulphur
One of miscellaneous anthrone, 2,4- diethyl thioxanthone, methyl o-benzoylbenzoate, methyl o-benzoylbenzoate are several
Kind.
4. according to UV Photocurable composition described in right 1, which is characterized in that the alkenes unsaturated group prepolymer includes epoxy
Acrylic resin, polyurethane acrylic resin, polyester acrylate resin, polyoxyalkylene acrylate resin, pure acrylate resin, ethylene
Base resin or their any mixture.
5. according to UV Photocurable composition described in right 1, which is characterized in that the alkenes unsaturated group monomer classification includes third
Olefin(e) acid Arrcostab, methacrylic acid hydroxy ester, (methyl) acrylate with cyclic structure or phenyl ring, the dilution of vinyl activity
Agent, glycols diacrylate, propandiols diacrylate, other glycols diacrylates, polyfunctional group activity are dilute
Release agent, alkoxylated acrylate, acrylic acid two dislike luxuriant ester, alkoxylated bis-phenol A bis- (methyl) acrylate, vinyl ethers
Reactive diluent, (methyl) acrylate of the end group containing methoxy, phosphorous flame retardant acrylate.
6. UV Photocurable composition according to claim 5, which is characterized in that the alkenes unsaturated group monomer is selected from third
The different monooctyl ester of olefin(e) acid (2-EHA), isodecyl acrylate (IDA), lauryl acrylate (LA), glycidyl methacrylate
(GMA), isobornyl methacrylate (IBOA), phenoxyethyl acrylate (POEA), 1,4-butanediol diacrylate
(BDDA), 1,6 hexanediol diacrylate (HDDA), phthalic acid diethanol diacrylate (PDDA), diethylene glycol two
Acrylate (DEGDA), triethylene glycol diacrylate (TEGDA), pentaerythritol triacrylate (PETA), pentaerythrite four
Acrylate (PETTA), two contracting trimethylolpropane tetra-acrylate (DTNPTA) polyethyleneglycol diacrylates (PEGDA),
Neopentylglycol diacrylate (NPGDA), two contracting propylene glycol double methacrylates (DPGDA), double pentaerythritol methacrylate
(DPHA) double pentaerythritol C5 methacrylate (DPPA), triethoxy trimethylolpropane trimethacrylate (3EOTMPTA),
One or more of trimethylolpropane trimethacrylate (TMPTA), tri (propylene glycol) diacrylate (TPGDA).
7. according to UV Photocurable composition described in right 1, which is characterized in that other auxiliary agents include sensitizer, filler, face
Material, levelling agent, dispersing agent, defoaming agent, polymerization inhibitor or their any mixture.
8. according to UV Photocurable composition described in right 7, which is characterized in that
The sensitizer is pyrazoline compounds, acridine compound, anthracene compound, coumarin kind compound or tertiary amines
Compound.
The filler includes talcum powder, silica, calcene, barium sulfate and kaolin；
The pigment includes white pigment, black pigment, color pigment；It specifically can be titanium dioxide, carbon black, phthalocyanine blue, pigment
Red, pigment yellow, phthalocyanine green, forever solid orange, solid palm fibre and phthalocyanine are purple forever；
The levelling agent includes polyacrylate, modified cellulose, organic silicone grease and fluorocarbon resin；
The dispersing agent includes that high molecular polymer, electroneutral polyamide and polyester mixture, low molecular weight unsaturated carboxylic acid are poly-
Close object, the copolymer containing acidic-group, the alkyl ammonium salt of the block copolymer containing acidic-group, urethane derivative and poly- third
Olefin(e) acid ester；
The defoaming agent includes organic silicon modified by polyether, higher alcohols, dimethyl silicone polymer；
The polymerization inhibitor includes quinhydrones, Hydroquinone monomethylether, hydroquinone, p-hydroxyanisole.
9. UV Photocurable composition according to claim 1, which is characterized in that the composition is suitable for photocuring system, main
To be suitable for UV curing system, be particularly suitable for UV curable ink and coating system.
10. UV Photocurable composition according to claim 1, which is characterized in that the composition is after body surface film
It is formed through ultraviolet source radiation curing, wherein the ultraviolet source can be high-pressure sodium lamp light source, is also possible to UV-LED light source；
The ultraviolet source wave-length coverage can be 200nm-500nm.
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Application publication date: 20190517 |