JP2880845B2 - UV curable ink - Google Patents
UV curable inkInfo
- Publication number
- JP2880845B2 JP2880845B2 JP3268592A JP3268592A JP2880845B2 JP 2880845 B2 JP2880845 B2 JP 2880845B2 JP 3268592 A JP3268592 A JP 3268592A JP 3268592 A JP3268592 A JP 3268592A JP 2880845 B2 JP2880845 B2 JP 2880845B2
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- modified
- diacrylate
- odor
- ink
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 20
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 229920000180 alkyd Polymers 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000976 ink Substances 0.000 description 14
- 235000019645 odor Nutrition 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 7
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- -1 polyol acrylate Chemical class 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 2
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 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 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical class C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- PTJDGKYFJYEAOK-UHFFFAOYSA-N 2-butoxyethyl prop-2-enoate Chemical compound CCCCOCCOC(=O)C=C PTJDGKYFJYEAOK-UHFFFAOYSA-N 0.000 description 1
- AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- IXPWKHNDQICVPZ-UHFFFAOYSA-N 2-methylhex-1-en-3-yne Chemical compound CCC#CC(C)=C IXPWKHNDQICVPZ-UHFFFAOYSA-N 0.000 description 1
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical class C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 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
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- CUOGLZPRZOICFY-UHFFFAOYSA-N CC(C)(C)NC(=C)C(O)=O Chemical compound CC(C)(C)NC(=C)C(O)=O CUOGLZPRZOICFY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- YCCCTDWBNCWPAX-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C1=CC=CC=C1C(O)=O Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C1=CC=CC=C1C(O)=O YCCCTDWBNCWPAX-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
- PSSYEWWHQGPWGA-UHFFFAOYSA-N [2-hydroxy-3-[2-hydroxy-3-(2-hydroxy-3-prop-2-enoyloxypropoxy)propoxy]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COCC(O)COCC(O)COC(=O)C=C PSSYEWWHQGPWGA-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- LKFAPHHHWRMPGC-UHFFFAOYSA-N butan-1-ol prop-2-enoic acid Chemical compound CCCCO.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C LKFAPHHHWRMPGC-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QKQSRIKBWKJGHW-UHFFFAOYSA-N morpholine;prop-2-enoic acid Chemical compound OC(=O)C=C.C1COCCN1 QKQSRIKBWKJGHW-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- WZESLRDFSNLECD-UHFFFAOYSA-N phenyl prop-2-eneperoxoate Chemical compound C=CC(=O)OOC1=CC=CC=C1 WZESLRDFSNLECD-UHFFFAOYSA-N 0.000 description 1
- MFTPIWFEXJRWQY-UHFFFAOYSA-N phosphoric acid prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OP(O)(O)=O MFTPIWFEXJRWQY-UHFFFAOYSA-N 0.000 description 1
- AJFJJTYOLHZAIE-UHFFFAOYSA-N phosphoric acid;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OP(O)(O)=O AJFJJTYOLHZAIE-UHFFFAOYSA-N 0.000 description 1
- WDHYRUBXLGOLKR-UHFFFAOYSA-N phosphoric acid;prop-2-enoic acid Chemical class OC(=O)C=C.OP(O)(O)=O WDHYRUBXLGOLKR-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Description
【0001】[0001]
【産業上の利用分野】本発明は、スクリーン印刷や他の
一般印刷に用いられる紫外線硬化型インキに関する。The present invention relates to a ultraviolet ray hardening type ink used in the screen printing or other common printing.
【0002】[0002]
【従来の技術】従来、スクリーン印刷に用いられる紫外
線硬化型スクリーンインキにおいては、 1)希釈剤として粘度を下げるため、 2)被印刷体への接着性を確保するため、 3)硬化塗膜に柔軟性を与えるため、 等を目的としてN−ビニル−2−ピロリドン(N−V−
2−P)が、各種の光反応性オリゴマーとの組み合わせ
で、あるいは各種の光反応性オリゴマー及び各種光反応
性希釈剤との組み合わせで用いられている。2. Description of the Related Art Ultraviolet light conventionally used for screen printing
In line hardening type screen ink, 1) for decreasing the viscosity as a diluent, 2) to ensure the adhesion to the printing material, 3) for providing flexibility to the cured coating film, N and the like for the purpose -Vinyl-2-pyrrolidone (N-V-
2-P) is used in combination with various photoreactive oligomers or in combination with various photoreactive oligomers and various photoreactive diluents.
【0003】[0003]
【発明が解決しようとする課題】しかしながら、N−ビ
ニル−2−ピロリドンにあっては、その物性として臭気
が大きく、また、人体に対する安全衛生面でも好ましく
ない。したがって、このN−ビニル−2−ピロリドンを
前記組み合わせにより紫外線硬化型スクリーンインキに
用いると、臭気によりインキ取扱者に不快感を生ぜしめ
るのみならず、安全衛生面においても懸念が伴うもので
あった。However, N-vinyl-2-pyrrolidone has a large odor as a physical property, and is not preferable in terms of safety and health for the human body. Therefore, using this N- vinyl-2-pyrrolidone to ultraviolet ray hardening type screen ink by the combination, not only causing a discomfort to the ink handlers by odor, accompanied concerns also in safety and health there were.
【0004】本発明は、このような従来の実情に鑑みて
なされたものであり、N−ビニル−2−ピロリドンを用
いることなく、所要の粘度、被印刷体への接着性、硬化
塗膜への柔軟性の付与等が得られる紫外線硬化型インキ
を提供することを目的とするものである。[0004] The present invention has been made in view of such conventional circumstances, and does not use N-vinyl-2-pyrrolidone, but has the required viscosity, adhesiveness to a printing medium, and cured coating film. it is an object to provide a ultraviolet ray hardening type ink such as addition of flexibility.
【0005】[0005]
【課題を解決するための手段】前記課題を解決するため
に本発明にあっては、ポリエステルアクリレート、ポリ
エーテルアクリレート、エポキシアクリレート、アルキ
ッドアクリレートのいずれかを含みビニルカプロラクタ
ム(VCL)を希釈剤として配合することにより、N−
ビニル−2−ピロリドンを配合した従来インキと同等の
性能、物性を有する紫外線硬化型スクリーンインキある
いは一般インキを得るに至った。ここで、ビニルカプロ
ラクタムは下記化学構造で示される。According to the present invention, there is provided a polyester acrylate,
Ether acrylate, epoxy acrylate, alk
N-acrylate by containing vinylcaprolactam (VCL) as a diluent
An ultraviolet curable screen ink or a general ink having the same performance and physical properties as conventional inks containing vinyl-2-pyrrolidone has been obtained. Here, vinyl caprolactam is represented by the following chemical structure.
【0006】[0006]
【化1】 また、本発明の配合例を下記表に示す。Embedded image Tables below show examples of the composition of the present invention.
【表1】 [Table 1]
【0007】ここで、VCLの望ましい配合量範囲は5
〜50重量部であり、特に望ましい配合量範囲は5〜3
0重量部である。また、紫外線硬化型スクリーンインキ
におけるVCLの使用範囲が1〜95重量部であるの
は、光開始剤の配合が必要であるためである。さらに、
表1の個々の配合物について具体的に示すと下記のとお
りである。 ・光反応性オリゴマーとしては、ポリウレタンアクリレ
ート、ポリエステルアクリレート、ポリエーテルアクリ
レート、エポキシアクリレート、オリゴアクリレート、
アルキッドアクリレート、ポリオールアクリレート、な
どが用いられる。 ・光反応性希釈剤としては、長鎖脂肪族アクリレート、
アリルアクリレート、ベンジルアクリレート、ブトキシ
エチルアクリレート、ブタンジオールモノアクリレー
ト、t−ブチルアミノアクリレート、カプロラクタムア
クリレート、ヒドロキシプロピルアクリレート、シアノ
エチルアクリレート、シクロヘキシルアクリレート、シ
クロペンタニルアクリレート、N,N−ジエチルアミノ
エチルアクリレート、2−エトキシエチルアクリレー
ト、グロセロールアクリレート、グリシジルアクリレー
ト、イソボロニルアクリレート、イソデシルアルアクリ
レート、イソオクチルアクリレート、ラウリルアクリレ
ート、モルホリンアクリレート、フェノキシアクリレー
ト、EO変性リン酸アクリレート、EO変性フタル酸ア
クリレート、ポリエチレングリコールアクリレート、ポ
リプロピレングリコールアクリレート、ステアリルアク
リレート、ビニルアセテート、アクリル化イソシアネー
ト、ビスフェノールAジアクリレート、EO変性ビスフ
ェノールAジアクリレート、EO変性ビスフェノールF
ジアクリレート、1,4−ブタンジオールジアクリレー
ト、1,3−ブチレングリコールジアクリレート、シク
ロペンタニルジアクリレート、ジエチレングリコールジ
アクリレート、EO変性ジエチレングリコールジアクリ
レート、ジペンタエリスリトールヘキサアクリレート、
アルキル変性ジペンタエリスリトールテトラアクリレー
ト、アルキル変性ジペンタエリスリトールトリアクリレ
ート、カプロラタム変性ジペンタエリスリトールヘキサ
アクリレート、ジトリメチロールプロパンテトラアクリ
レート、ECH変性エチレングリコールジアクリレー
ト、グリセロールアクリレート、ECH変性グリセロー
ルトリアクリレート、1,6−ヘキサンジオールジアク
リレート、長鎖脂肪族ジアクリレート、エトキシ化シク
ロヘキシルジアクリレート、ネオペンチルグリコールジ
アクリレート、ペンタエリスリトールトリアクリレー
ト、ペンタエリスリトールテトラアクリレート,EO変
性リン酸ジアクリレート、EO変性リン酸トリアクリレ
ート、ECH変性フタル酸ジアクリレート、ポチエチレ
ングリコールジアクリレート、ポリプロピレングリコー
ルジアクリレート、テトラエチレングリコールジアクリ
レート、トリエチレングリコールジアクリレート、トリ
エチレングリコールジビニルエーテル、トリグリセロー
ルジアクリレート、ネオペンチルグリコール変性トリメ
チロールプロパントリアクリレート、トリメチロールプ
ロパントリアクリレート、EO変性トリメチロールプロ
パントリアクリレート、PO変性トリメチロールプロパ
ントリアクリレート、ECH変性トリメチロールプロパ
ントリアクリレート、トリプロピレングリコールジアク
リレート、トリス(アクリロキシエチル)イソシアネー
ト、カプロラクタム変性トリス(アクリロキシエチル)
イソシアネート、及び、これらのアクリレート部分がメ
タアクリレートになったものが用いられる。Here, the desirable compounding amount range of VCL is 5
To 50 parts by weight, and a particularly desirable compounding amount range is 5 to 3 parts by weight.
0 parts by weight. The reason why the usage range of the VCL in the ultraviolet-curable screen ink is 1 to 95 parts by weight is that it is necessary to mix a photoinitiator. further,
The specific formulations of Table 1 are as follows. -As photoreactive oligomers, polyurethane acrylate, polyester acrylate, polyether acrylate, epoxy acrylate, oligo acrylate,
Alkyd acrylate, polyol acrylate, and the like are used. -As a photoreactive diluent, long-chain aliphatic acrylate,
Allyl acrylate, benzyl acrylate, butoxyethyl acrylate, butanediol monoacrylate, t-butylaminoacrylate, caprolactam acrylate, hydroxypropyl acrylate, cyanoethyl acrylate, cyclohexyl acrylate, cyclopentanyl acrylate, N, N-diethylaminoethyl acrylate, 2-ethoxy Ethyl acrylate, glycerol acrylate, glycidyl acrylate, isobornyl acrylate, isodecyl acrylate, isooctyl acrylate, lauryl acrylate, morpholine acrylate, phenoxy acrylate, EO-modified phosphate acrylate, EO-modified phthalic acrylate, polyethylene glycol acrylate, Polypropylene glycol Acrylate, stearyl acrylate, vinyl acetate, acrylated isocyanates, bisphenol A di acrylate, EO-modified bisphenol A di acrylate, EO-modified bisphenol F
Diacrylate, 1,4-butanediol diacrylate, 1,3-butylene glycol diacrylate, cyclopentanyl diacrylate, diethylene glycol diacrylate, EO-modified diethylene glycol diacrylate, dipentaerythritol hexaacrylate,
Alkyl-modified dipentaerythritol tetraacrylate, alkyl-modified dipentaerythritol triacrylate, caprolatum-modified dipentaerythritol hexaacrylate, ditrimethylolpropane tetraacrylate, ECH-modified ethylene glycol diacrylate, glycerol acrylate, ECH-modified glycerol triacrylate, 1,6- Hexanediol diacrylate, long-chain aliphatic diacrylate, ethoxylated cyclohexyl diacrylate, neopentyl glycol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, EO-modified phosphate diacrylate, EO-modified phosphate triacrylate, ECH-modified Phthalic acid diacrylate, polyethylene glycol diacrylate , Polypropylene glycol diacrylate, tetraethylene glycol diacrylate, triethylene glycol diacrylate, triethylene glycol divinyl ether, triglycerol diacrylate, neopentyl glycol-modified trimethylolpropane triacrylate, trimethylolpropane triacrylate, EO-modified triacrylate Methylolpropane triacrylate, PO-modified trimethylolpropane triacrylate, ECH-modified trimethylolpropane triacrylate, tripropylene glycol diacrylate, tris (acryloxyethyl) isocyanate, caprolactam-modified tris (acryloxyethyl)
Isocyanates and those in which these acrylate moieties have become methacrylate are used.
【0008】・光開始剤としては、ベンゾイン系、ベン
ゾフェノン系、アセトフェノ系、チオキサントン系、特
殊系、などが用いられる。 ・光増感剤としては、脂肪族アミン系、芳香族アミン
系、などが用いられる。 ・添加剤としては、泡消性、被印刷物上でのレベリング
性、メッシュ孔通過性、転写インキの版離れ性などの流
動性調整剤として、シリコン樹脂、シリコンオイル、水
酸基を付加したシリコン、ポリシロキサン化合物、アク
リルオリゴマーによる界面活性剤、フッ素系界面活性
剤、などが用いられる。[0008] As the photoinitiator, benzoin type, benzophenone type, acetopheno type, thioxanthone type, special type, etc. are used. -As the photosensitizer, an aliphatic amine type, an aromatic amine type, or the like is used.・ Additives include silicone resin, silicone oil, hydroxyl-added silicone, and polyhydric acid as fluidity regulators such as defoaming property, leveling property on the printed material, mesh hole passing property, and transfer ink release property. A siloxane compound, a surfactant based on an acrylic oligomer, a fluorine-based surfactant, or the like is used.
【0009】また、目的、用途に応じて、安定剤、紫外
線吸収剤、艶消し剤、ブロッキング防止剤などが用いら
れる。 ・着色、体質顔料としては、有機、無機の着色顔料、印
刷適性付与や流動性調整のための体質顔料、などが目
的、用途に応じて用いられる。Further, stabilizers, ultraviolet absorbers, matting agents, antiblocking agents and the like are used according to the purpose and application. As coloring and extender pigments, organic and inorganic color pigments, extender pigments for imparting printability and adjusting fluidity, and the like are used according to the purpose and application.
【0010】[0010]
【実施例】以下の表2に本発明の実施例1〜3と、実施
例1〜3に対応する比較例1〜3の配合を示すととも
に、表3にその特性評価を示す。EXAMPLES Table 2 below shows the formulations of Examples 1 to 3 of the present invention and Comparative Examples 1 to 3 corresponding to Examples 1 to 3, and Table 3 shows the evaluation of the characteristics.
【0011】[0011]
【表2】 [Table 2]
【表3】 [Table 3]
【0012】なお、実施例1〜3と比較例1〜3とは、
紫外線で200ミリジュール/cm2のエネルギーにて
硬化させたものであり、膜圧は15ミクロンとした。Examples 1 to 3 and Comparative Examples 1 to 3
Der those cured by energy of 200 millijoules / cm2 ultraviolet is, film thickness was 15 microns.
【0013】実施例1は、対応する比較例1がN−V−
2−Pを30.0重量%配合したのに対し、N−V−2
−Pを配合することなくこれに代えてVCLを30.0
重量%配合したものである。そして、この実施例1と比
較例1との特性評価において、比較例1は臭気を除く他
の項目が「良」であって臭気が「不良」であるのに対
し、実施例1は臭気を含む全ての項目が「良」となり、
よって、他の項目に対する評価を「良」に維持しつつ臭
気に関して改善し得ることが判明した。In Example 1, the corresponding comparative example 1 is NV-
While NV was blended at 30.0% by weight, NV-2
VCL was changed to 30.0 instead of -P.
% By weight. In the evaluation of the characteristics of Example 1 and Comparative Example 1, Comparative Example 1 showed that the other items except for the odor were “good” and the odor was “bad”, whereas Example 1 showed the odor. All items including "good"
Therefore, it was found that the odor can be improved while maintaining the evaluation of other items at “good”.
【0014】実施例2は、対応する比較例2がN−V−
2−Pを20.0重量%配合したのに対し、N−V−2
−Pを配合することなくこれに代えてVCLを20.0
重量%配合したものである。そして、この実施例2と比
較例2との特性評価において、比較例2は臭気が「不
良」、PVCでの折曲げ性が「中間」、他の項目が
「良」であるのに対し、実施例2は臭気が「良」とな
り、他の項目に対する評価を低下させることなく臭気に
関して改善し得ることが判明した。In Example 2, the corresponding Comparative Example 2 is NV-
2-P was added at 20.0% by weight, whereas NV-2
VCL instead of 20.0 without blending -P
% By weight. In the evaluation of the characteristics of Example 2 and Comparative Example 2, Comparative Example 2 has an odor of “poor”, a bending property of PVC of “medium”, and other items of “good”. In Example 2, the odor was “good”, and it was found that the odor could be improved without lowering the evaluation of other items.
【0015】実施例3は、対応する比較例3がTPGD
Aを30.0重量%配合したのに対し、TPGDAを2
0.0重量%にしてVCLを10.0重量%配合したも
のである。そして、この実施例3と比較例3との特性評
価において、比較例3はPCへの接着性が「不良」、P
VCへの接着性とPVCでの折曲げ性とが「中間」、臭
気と硬化性とが「良」であるのに対し、実施例3は全て
の項目が「良」となり、臭気及び硬化性に対する評価を
低下させることなくPCへの接着性、PVCへの接着
性、PVCでの折曲げ性に関して改善し得ることが判明
した。In Example 3, the corresponding comparative example 3 is TPGD
A was added at 30.0% by weight, while TPGDA was added at 2%.
VCL was added at 10.0% by weight to 0.0% by weight. In the evaluation of the characteristics of Example 3 and Comparative Example 3, Comparative Example 3 showed that the adhesiveness to PC was “poor” and P
While the adhesiveness to VC and the bendability with PVC are “intermediate” and the odor and curability are “good”, in Example 3, all items are “good”, and the odor and curability It has been found that the adhesiveness to PC, the adhesiveness to PVC, and the bendability with PVC can be improved without lowering the evaluation of.
【0016】[0016]
【発明の効果】以上説明したように本発明よれば、ポリ
エステルアクリレート、ポリエーテルアクリレート、エ
ポキシアクリレート、アルキッドアクリレートのいずれ
かを含みビニルカプロラクタムを希釈剤として配合し、
さらに他の光反応性希釈剤と併用配合し、若しくはこれ
らに流動性調整剤を加えた紫外線硬化型インキより、臭
気による不快感や人体に対する安全衛生面での懸念を伴
うことなく、従来の同等の性能及び物性の紫外線硬化型
インキが得られた。よって、性能及び物性を維持しつ
つ、臭気による不快感をインキ取扱者に与えることな
く、かつ、人体に対する安全衛生面でも好ましい紫外線
硬化型インキを提供することができた。As described above, according to the present invention, poly
Ester acrylate, polyether acrylate, d
Both oxyacrylate and alkyd acrylate
Or blended vinylcaprolactam as a diluent comprises,
Compared with conventional photo-reactive diluents, UV-curable inks with a fluidity modifier added to them without the discomfort caused by odors and the health and safety concerns of the human body. An ultraviolet curable ink having the properties and physical properties described above was obtained. Therefore, it was possible to provide an ultraviolet curable ink which maintains the performance and physical properties, does not give an unpleasant odor to an ink handler, and is also preferable in terms of safety and health for the human body.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6,DB名) C09D 11/00 - 13/00 C08F 290/00 - 290/14 C08F 299/00 - 299/08 ──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 6 , DB name) C09D 11/00-13/00 C08F 290/00-290/14 C08F 299/00-299/08
Claims (4)
ルアクリレート、エポキシアクリレート、アルキッドア
クリレートのいずれかを含みビニルカプロラクタムを希
釈剤として配合したことを特徴とする紫外線硬化型イン
キ。1. Polyester acrylate, polyether
Ruacrylate, epoxy acrylate, alkyd
Ultraviolet ray hardening type ink, wherein the formulated as a diluent vinylcaprolactam comprise any of the acrylate.
応性希釈剤と併用配合したことを特徴とする請求項1記
載の紫外線硬化型インキ。Wherein said vinyl caprolactam, claim 1 Symbol, characterized in that in combination blended with other photoreactive diluents
Ultraviolet ray hardening type ink placement.
とする請求項1記載の紫外線硬化型インキ。 3. The method according to claim 1, wherein a fluidity modifier is further added.
The ultraviolet curable ink according to claim 1, wherein
性希釈剤と併用配合するとともに、流動性調整剤を加え
たことを特徴とする請求項1記載の紫外線硬化型イン
キ。Wherein said vinyl caprolactam with combination blended with other photoreactive diluents, ultraviolet ray hardening type ink according to claim 1, wherein the addition of fluidity modifier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3268592A JP2880845B2 (en) | 1992-01-23 | 1992-01-23 | UV curable ink |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3268592A JP2880845B2 (en) | 1992-01-23 | 1992-01-23 | UV curable ink |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05202331A JPH05202331A (en) | 1993-08-10 |
| JP2880845B2 true JP2880845B2 (en) | 1999-04-12 |
Family
ID=12365732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3268592A Expired - Lifetime JP2880845B2 (en) | 1992-01-23 | 1992-01-23 | UV curable ink |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2880845B2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2660507B2 (en) * | 1985-05-31 | 1997-10-08 | 大日本インキ化学工業株式会社 | Coating agent |
| JP2812580B2 (en) * | 1991-04-23 | 1998-10-22 | 日本化薬株式会社 | Printing ink composition and cured product thereof |
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1992
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