JPH0510395B2 - - Google Patents
Info
- Publication number
- JPH0510395B2 JPH0510395B2 JP24609784A JP24609784A JPH0510395B2 JP H0510395 B2 JPH0510395 B2 JP H0510395B2 JP 24609784 A JP24609784 A JP 24609784A JP 24609784 A JP24609784 A JP 24609784A JP H0510395 B2 JPH0510395 B2 JP H0510395B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- diallyl phthalate
- varnish
- electron beam
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000010894 electron beam technology Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 16
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 15
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 15
- -1 vinyl compound-modified diallyl phthalate Chemical class 0.000 claims description 13
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 10
- 238000007639 printing Methods 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 42
- 239000002966 varnish Substances 0.000 description 22
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 6
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 5
- 238000001723 curing Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-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.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- YNTQTLGBCMXNFX-UHFFFAOYSA-N [5-ethyl-2-(2-methyl-1-prop-2-enoyloxypropan-2-yl)-1,3-dioxan-5-yl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(CC)COC(C(C)(C)COC(=O)C=C)OC1 YNTQTLGBCMXNFX-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- 238000001227 electron beam curing Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- NLPBRTBBFUOESW-UHFFFAOYSA-N 1-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)C(CC)OC(=O)C(C)=C NLPBRTBBFUOESW-UHFFFAOYSA-N 0.000 description 1
- GKZPEYIPJQHPNC-UHFFFAOYSA-N 2,2-bis(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.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GKZPEYIPJQHPNC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- ZBGXCNSKAFBJPP-UHFFFAOYSA-N 2-trimethylsilylprop-2-enoic acid Chemical compound C[Si](C)(C)C(=C)C(O)=O ZBGXCNSKAFBJPP-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 231100000987 absorbed dose Toxicity 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000077 silane Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
Description
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"Objective of the Invention" (Industrial Application Field) The present invention is capable of forming a coating film that is easily cured by electron beams and has excellent flexibility, solvent resistance, coating hardness, and adhesion to a substrate. The present invention relates to an electron beam curable printing ink composition. (Prior Art) In recent years, with advances in electron beam irradiation equipment, the use of electron beam curing methods has expanded to a wide range of fields, and a large number of electron beam curable coating compositions have been provided. Furthermore, there is an ultraviolet curing method that is relatively similar to this electron beam curing method. The ultraviolet curable coating composition is instantly cured by ultraviolet rays due to the combination of an acrylic oligomer, a monomer, and a photopolymerization initiator or a photoactivator (sensitizer). Therefore, it is possible to repurpose these compositions as electron beam curable coating compositions, but the photopolymerization initiator or photoactivator is
Almost no effect is expected, and oligomers,
It cannot be said that some monomers always form a good cured coating film upon electron beam irradiation. This is thought to be due to the essential difference between photochemical reactions caused by electromagnetic ultraviolet rays and radiation chemical reactions caused by charged particle electron beams. (Problems to be Solved by the Invention) The present invention is characterized in that it contains as main components a diallyl phthalate prepolymer or a vinyl compound-modified diallyl phthalate prepolymer, dipentaerythritol acrylate or a derivative thereof, and a diluent monomer. The purpose of the present invention is to provide a printing ink composition capable of obtaining a film having excellent flexibility, solvent resistance, coating hardness, and adhesion to a substrate. "Structure of the Invention" (Means for Solving the Problems) According to research by the present inventors, the main components are diallyl phthalate prepolymer or vinyl compound-modified diallyl phthalate prepolymer, dipentaerythritol acrylate or its derivative, and By including a diluent monomer, diallyl phthalate prepolymer or vinyl compound-modified diallyl phthalate prepolymer 1
It has been found that containing ~50% by weight, 10-70% by weight of dipentaerythritol acrylate or its derivative, and 1-40% by weight of diluent monomer is very effective in achieving the above-mentioned objectives. The present invention will be explained in more detail below. As the diallyl phthalate prepolymer used in the present invention, one represented by the following general formula and having a molecular weight of 1.000 to 20.000 is used. (Here, a is 0 to 2, R 1 is a hydrogen atom or a methyl group, and R 2 is an alkyl group having 1 to 18 carbon atoms, an amino group or a silane group). Examples of such compounds include diallyl phthalate prepolymers, which are polymers of diallyl phthalates such as diallyl orthophthalate and diallyl isophthalate. In addition, in the present invention, a compound obtained by modifying a diallyl phthalate prepolymer with a vinyl compound can also be used in combination with these diallyl phthalate prepolymers. Effective vinyl compounds include acrylic esters and methacrylic esters having alkyl groups, amino groups, silane groups, etc., such as methyl, ethyl, propyl, butyl, amyl, hexyl, 4-methyl-2-pentyl, and octyl. ,
Nonyl, decyl, stearyl acrylic ester or methacrylic ester, lactone-modified acrylate monomer (trade name Plaxel (manufactured by Daicel Chemical Industries, Ltd.), acrylamide, methacrylamide, N-methylolacrylamide, vinyltrimethoxysilane, vinyltriethoxy silane, tetravinylsilane, γ-methacryloxypropyltrimethoxysilane, α-trimethylsilylacrylic acid, vinyltrimethylsilane, etc. In the present invention, dipentaerythritol acrylate includes dipentaerythritol pentaacrylate, dipentaerythritol pentaacrylate, One or more types of pentaerythritol hexaacrylate etc. Also,
These derivatives include acrylate oligomers represented by the following general formula. Note that this derivative can be obtained, for example, by adding pivalic acid to dipentaerythritol and then esterifying it with acrylic acid. The diluent monomer in the present invention is not particularly limited as long as it is addition-polymerizable, such as acrylic acid or methacrylic acid or an ester thereof, such as ethyl (meth)acrylate, butyl (meth)acrylate, 2-(meth)acrylate, etc. Ethylhexyl;
Esters of polyhydric alcohols and acrylic acid and/or methacrylic acid, such as ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, trimethylolpropane (meth)acrylate, pentaerythritol tri(meth)acrylate, triacrylisocyanurate, vinylpyrrolidone, etc. In the present invention, dipentaerythritol acrylate or its derivatives and diluent monomers are included, but dipentaerythritol acrylate or its derivatives are rapidly curable with electron beams, so if dipentaerythritol acrylate or its derivatives are not used, Linear curing becomes slow. Furthermore, a composition containing only dipentaerythritol acrylate or its derivative as a monomer component has a high viscosity, making it difficult to form into an ink. Therefore, when adjusting the viscosity of ink, low viscosity monomers,
That is, diluent monomers are required. The present invention preferably comprises 1 to 50% by weight of diallyl phthalate prepolymer or vinyl compound-modified diallyl phthalate prepolymer, 10 to 70% by weight of dipentaerythritol acrylate or its derivative, and 1 to 40% by weight of diluent monomer. By adjusting the composition ratio, a printing ink composition having good fluidity as an ink, good electron beam curability and printability can be obtained. The electron beam curable printing ink composition of the present invention may optionally contain other resins such as epoxy resins, acrylic resins, polyester resins, pigments, dyes, etc.
Various additives, stabilizers, etc. can be added. The electron beam curable printing ink composition of the present invention is coated on various substrates such as paper, plastic films, metal plates, etc. in accordance with conventional methods, and then irradiated with electron beams to polymerize and cure, followed by drying. The electron beams used are Kotscroft-Walton type, Van de Graaff type,
Emitted from various electron beam accelerators such as resonant transformer type, insulated core transformer type, linear type, Dynamicron type, high frequency type, etc., it is 50 to 1000 KeV, preferably 100 to
An electron beam with an energy in the range of 300 KeV is used. While continuously running the coated base material,
By irradiating a continuous curtain-like electron beam from a linear filament, continuous curing of the coating layer becomes possible. EXAMPLES The present invention will be explained in more detail with reference to Examples below. In the examples, "parts" indicate parts by weight. Example 1 Varnish (1-1) was obtained by dissolving 30 parts of diallyl orthophthalate prepolymer (Daiso Tap A, manufactured by Osaka Soda Co., Ltd.) with 70 parts of dipentaerythritol hexaacrylate (DPHA manufactured by Nippon Kayaku Co., Ltd.). . Similarly, a varnish (1-2) was prepared using a resin diallyl orthophthalate prepolymer (Daiso Tap L, manufactured by Osaka Soda Co., Ltd.), and a varnish (1-3) was prepared using a diallyl isophthalate polymer (Daiso Tap, manufactured by Osaka Soda Co., Ltd.). I got it. As a comparative example, 30 parts of diode strip A-BPE
-4 (Bisphenol A ethylene oxide addition diacrylate, manufactured by Shin-Nakamura Chemical Co., Ltd.) 70 parts to make a varnish (1-4), and 30 parts of Diosodap dissolved in 70 parts of A-BPE-4 to make a varnish. (1-5) was obtained. Example 2 [2-1] Modification of diallyl phthalate prepolymer Diallyl orthophthalate prepolymer 35.33 was added in a reactor equipped with a reflux condenser and a stirrer.
and 35.33 parts of methyl ethyl ketone, and heated to 80°C in a nitrogen atmosphere. Add to this 4.59 parts of stearyl acrylate and benzoyl peroxide.
A mixed solution of 0.19 parts of methyl ethyl ketone and 24.56 parts of methyl ethyl ketone was added dropwise little by little over 30 minutes while stirring and maintaining the temperature at 80°C. One hour after the completion of the dropwise addition, 0.2 part of hydroquinone was added, and methyl ethyl ketone was removed under reduced pressure to obtain resin [2-1]. [2-2] Modification of diallyl phthalate prepolymer Using the same equipment as in [2-1], 38.39 parts of diallyl orthophthalate prepolymer and 38.39 parts of methyl ethyl ketone are charged and heated to 80°C in a nitrogen atmosphere. To this, 1.54 parts of N-methylolacrylamide, 0.19 parts of α,α-azobisisobutyronitrile, and 21.5 parts of methyl ethyl ketone.
Part of the mixed solution was added dropwise in the same manner as [2-1], and methyl ethyl ketone was distilled under reduced pressure to obtain the resin [2-1].
2] was obtained. [2-3] Modification of diallyl phthalate prepolymer Using the same equipment as in [2-1], 36.3 parts of diallyl isophthalate prepolymer and 36.3 parts of methyl ethyl ketone were added, and the mixture was heated at 80°C in a nitrogen atmosphere.
Heat until. A mixed solution of 3.63 parts of α-methacryloxypropyltrimethoxysilane, 0.2 parts of benzoyl peroxide, and 23.57 parts of methyl ethyl ketone was added dropwise to this in the same manner as in [2-1], and methyl ethyl ketone was distilled under reduced pressure to obtain resin [2-3]. Obtained. [2-4] Modification of diallyl phthalate prepolymer Using the same equipment as in [2-1], 27.9 parts of diallyl orthophthalate prepolymer and 27.9 parts of methyl ethyl ketone were added, and the mixture was heated to 80% in a nitrogen atmosphere.
Heat to â. A mixed solution of 12.0 parts of Plaxel FA-3 (manufactured by Daicel Chemical Industries, Ltd.), 0.2 parts of benzoyl peroxide, and 22.0 parts of methyl ethyl ketone was added dropwise to this in the same manner as in [2-1], and the methyl ethyl ketone was distilled under reduced pressure to form the resin [2]. -4] was obtained. 15 parts of the resin [2-1] obtained in [2-1] and 15 parts of Diisoisodap were dissolved in 70 parts of dipentaerythritol hexaacrylate, and the varnish (2-1) was dissolved in 70 parts of dipentaerythritol hexaacrylate.
-1) was obtained. In the same way, varnish (2-2) was added to resin [2-2].
2), varnish (2-3) was obtained from resin [2-3], and varnish (2-4) was obtained from resin [2-4]. As a comparative example, Epicoat 828 (epoxy resin,
Varnish (2-5) was obtained by dissolving 30 parts of a resin obtained by esterifying Yuka Ciel Epoxy Co., Ltd.) with acrylic acid in 70 parts of dipentaerythritol hexaacrylate. Similarly, varnish (2-
6) was obtained. Example 3 30 parts of the resin used in Example 1 was mixed with DPCA-30 (manufactured by Nippon Kayaku Co., Ltd.) Varnish (3-1) and Varnish (3-1) were dissolved in Example 1 to obtain a varnish.
2), varnish (3-3) was obtained. As a comparative example, 30 parts of a resin obtained by esterifying Epicote 828 with acrylic acid was used as DPCA-30 70
A varnish (3-4) was obtained. Similarly, 30 parts of a resin obtained by esterifying Epicote 1001 with acrylic acid was dissolved in 70 parts of DPCA-30 to obtain a varnish (3-5). Example 4 Using the varnishes obtained in Examples 1, 2, and 3, an ink for offset printing was produced. The ink formulation is shown below. Yellow ink formulation Lionol Yellow FGN (pigment manufactured by Toyo Ink Manufacturing Co., Ltd.) 13.5 parts Alumina white 6 parts Talc 5 parts Varnish 40 parts A-BPE-4 * 35.5 parts (*) Bisphenol A ethylene oxide addition diacrylate (Shin Nakamura (Manufactured by Kagaku Co., Ltd.) Red ink formulation #781 Brilliant Carmine 6BG (Pigment manufactured by Toyo Ink Manufacturing Co., Ltd.) 18 parts Talc 5 parts Varnish 39 parts KAYARAD R-604* 38 parts *KAYARAD R-604 Blue ink formulation Lionor Blue GLA (pigment manufactured by Toyo Ink Manufacturing Co., Ltd.) 20 parts Talc 5 parts Varnish 45 parts Photomer 4149 * 30 parts * Photomer 4149 Diamond Shamzock diluted monomer black ink prescription Mitsubishi Carbon MA-7 (Mitsubishi Kasei Corporation) 10 parts Lionogen Violet RL (pigment manufactured by Toyo Ink Manufacturing Co., Ltd.) 2 parts Shinin Blue PRPC (pigment manufactured by Toyo Ink Manufacturing Co., Ltd.) 3 parts Alumina White 3 parts Varnish 40 parts OTA 480* 42 parts * OTA480 UCb Chemical Diluted Momanar manufactured by sector Each color ink manufactured in Example 4 was
The test piece was printed on carton paper using a tester, used as a printed test piece, and this test piece was adhered to a traveling film using double-sided tape and passed under an electron beam irradiation device to obtain a cured film. The electron beam irradiation equipment used to prepare the test pieces was
Acceleration voltage 175Kev, absorbed dose using curtain-type electron beam irradiation device manufactured by Energy Sciences, Inc. (ESI)
3Mrad, oxygen concentration in the atmosphere under the irradiation device is 300ppm
It is as follows. Using the test pieces obtained by the above method, the flexibility was compared by (1) cracking of the coating film by a 180° bending test. (2) 5 cm of cloth impregnated with methyl ethyl ketone
After rubbing back and forth with a cloth, the ink film was rubbed off and the solvent resistance was compared. (3) Using a 6B to 6H pencil, the hardness of the coating was compared by pressing the tip of the pencil forward at a 45° angle and observing whether the coating was cut or gouged. (4) Using 18 mm of cellophane manufactured by Nichiban, the cellophane tape was attached to the test piece and then instantly peeled off at 90 degrees, and the adhesion was evaluated by observing the state of peeling and comparing the adhesion. The results are shown in the table.
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çã®åŒå®³ã¯èŠãããªãå©ç¹ãããã[Table] "Effects of the Invention" As described above, the electron beam curable printing ink composition of the present invention contains a diallyl phthalate prepolymer or a vinyl compound-modified diallyl phthalate prepolymer, dipentaerythritol acrylate or a derivative thereof, and a diluent monomer. By containing it as a main component, it forms a film with excellent flexibility, solvent resistance, coating hardness, and adhesion to the substrate.In addition, since it is electron beam cured, it is not suitable for ultraviolet curable films. There is no coloring caused by commonly seen photoactivators (sensitizers), and since the strong penetrating power of electron beams is used, there are problems such as curing inhibition effects from pigments, plasticizers, and other additives. has advantages that cannot be seen.
Claims (1)
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第ïŒé èšèŒã®é»åç·ç¡¬ååå°å·ã€ã³ãçµæç©ã[Scope of Claims] 1. An electron beam curable printing ink composition comprising as main components a diallyl phthalate prepolymer or a vinyl compound-modified diallyl phthalate prepolymer, dipentaerythritol acrylate or a derivative thereof, and a diluent monomer. 2. Claim 1 comprising 1 to 50% by weight of diallyl phthalate prepolymer or vinyl compound-modified diallyl phthalate prepolymer, 10 to 70% by weight of dipentaerythritol acrylate or its derivative, and 1 to 40% by weight of diluent monomer. electron beam curable printing ink composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59246097A JPS61126179A (en) | 1984-11-22 | 1984-11-22 | Electron beam curing coating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59246097A JPS61126179A (en) | 1984-11-22 | 1984-11-22 | Electron beam curing coating composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61126179A JPS61126179A (en) | 1986-06-13 |
| JPH0510395B2 true JPH0510395B2 (en) | 1993-02-09 |
Family
ID=17143442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59246097A Granted JPS61126179A (en) | 1984-11-22 | 1984-11-22 | Electron beam curing coating composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61126179A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS515423A (en) * | 1974-06-27 | 1976-01-17 | Esu Ei Efu Gaado Shisutemusu I | Ben oyobi futasochi |
| JPS53104638A (en) * | 1977-02-23 | 1978-09-12 | Mitsubishi Rayon Co Ltd | Coating composition and preparation of abrasion resistant synthetic resin molded artticle using the same |
| JPS5921646A (en) * | 1982-06-25 | 1984-02-03 | Nippon Kayaku Co Ltd | Ethylenically unsaturated compound and preparation thereof |
| JPS60115608A (en) * | 1983-11-25 | 1985-06-22 | Sanken Kako Kk | Thermosetting resin composition |
-
1984
- 1984-11-22 JP JP59246097A patent/JPS61126179A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS515423A (en) * | 1974-06-27 | 1976-01-17 | Esu Ei Efu Gaado Shisutemusu I | Ben oyobi futasochi |
| JPS53104638A (en) * | 1977-02-23 | 1978-09-12 | Mitsubishi Rayon Co Ltd | Coating composition and preparation of abrasion resistant synthetic resin molded artticle using the same |
| JPS5921646A (en) * | 1982-06-25 | 1984-02-03 | Nippon Kayaku Co Ltd | Ethylenically unsaturated compound and preparation thereof |
| JPS60115608A (en) * | 1983-11-25 | 1985-06-22 | Sanken Kako Kk | Thermosetting resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61126179A (en) | 1986-06-13 |
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